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Charles William Shoppee 1904-1994

Written by Lewis N. Mander.

Introduction

Charles Shoppee was a major figure in research conducted on the steroid family of organic compounds. After an extensive grounding in mechanistic organic chemistry with such major figures as Sir Jocelyn Thorpe FRS at Imperial College and Sir Christopher Ingold FRS at the University of Leeds, Shoppee spent the war years in Basel working with Tadeus Reichstein. There, he commenced to apply reaction mechanistic concepts to the reactions of natural products, particularly steroids where he was in the vanguard of a huge and widespread activity prompted, in part, by the pharmaceutical industry's interests in these important compounds. In additional to their therapeutic potential, however, they provided a rigid template on which one could explore aspects of structure determination, synthesis, mechanism and stereochemistry. After the war, Shoppee spent a brief period in London before taking up the chair of chemistry at the University of Wales, Swansea, where he built up the research strengths of the Chemistry Department and continued to build a major opus on the synthesis, stereochemistry and physical-organic chemistry of steroids during the following eight years. These interests were continued for a further 13 years at the University of Sydney up until his formal retirement in 1969. After a period of five years at Texas Technological University, he returned to Australia and maintained his commitment to science until the end, still working at the bench in his 87th year.

Early years

Charles Shoppee was born on 4 February 1904, at Crouch End (a northern suburb of London), the elder son of Joseph William and Emma Elizabeth Shoppee (née Hawkswell of York). Charles's younger brother, Stanley Shoppee, FCA, predeceased him in 1967. The family was descended from the noble French family of Chappuis, and could trace its ancestry back to 1109. The male members of the family were generally pillars of the Church or lawyers – often Clerk of the Parlement at Lyon, although Louis Chappuis was created Marquis de Mirebel by letters patent of Louis XV of France in 1746. An earlier, female member of the family was distinguished by her descendants, being the great-grandmother of Armand Jean du Plessis, Cardinal Duc de Richelieu, and the great-great-grandmother of the Duc de Villars, Marshal of France.

Although Joseph Shoppee was only four years old when his own father died, he nevertheless went on to King's College, London, where he won several prizes. After two years, however, financial circumstances caused him to enter the office of John K. Gilliat and Company of 7 Crosby Square, London. There he remained for the rest of his life (d. 15 August 1944), eventually becoming secretary to the company. Joseph Shoppee was a man of varied intellectual attainments; readily reading French and German, he rapidly learnt Spanish when his company entered the Costa Rica coffee market. Although he had not looked at conic sections and trigonometry for some 35 years, he still knew these subjects well when Charles encountered them. The father was interested in French, German and Italian medieval history, and was well acquainted with medieval architecture – he had visited every cathedral in England and Wales several times. As a species of counterweight to this medievalism, he was also interested in the topography of the railways of England, Scotland and Wales. Thus, Charles grew up in a stimulating environment.

At the age of 10, Charles went to the Stationers' Company's School where he flourished. He eventually became captain of football, captain of cricket, sergeant-major of the Officer Training Corps, School organist, head prefect, and captain of the school. Around the age of 13, he showed promising talent as a pianist and could 'struggle' (his words) through the Scherzo in B flat minor (op. 31) of Chopin. He studied with Dr R. Walker Robson, acquired the Matthey technique, and gradually became acquainted with some of the works of Bach, Mozart, Beethoven, Chopin, Schumann, Liszt, Brahms, Cesar Franck, Scriabin, and Rachmaninov. At school, he was greatly influenced by two of the masters, A.E. Richards, BA (Cantab) (Mathematics) and F.T. Addyman, BSc (Lond), FRIC (Chemistry), eventually passing the Intermediate Examination of the University of London with Honours in 1921.

On leaving school in 1921, Oxford or Cambridge being financially impossible, Shoppee went to Imperial College (Royal College of Science), where he obtained the ARCS in 1923 and majored in chemistry with 1st Class Honours. In his year were H.J. Emeleus and R.P. Linstead, both later to be elected to the Royal Society of London, as was Charles. During the years 1923-24, he became a research student of Sir Jocelyn Thorpe, FRS, and tried to repeat some work on citraconic anhydride said to yield a cyclobutane compound. In fact, the main product, derived by three carbon tautomerism from itaconic anhydride, was a derivative of cyclopentane. During his years at College, Charles played association football (soccer) for the Royal College of Science and Imperial College, and cricket for the Highgate Cricket Club. He also managed to continue playing the piano and the organ and even managed to earn some useful pocket money by taking services when the church organist was absent on his summer holiday.

Early career

In 1924, Christopher Ingold, FRS, was elected to the Chair of Organic Chemistry at the University of Leeds and invited Shoppee to accompany him, obtaining for him a DSIR Grant of £120 per annum. Charles's mother had been, prior to her marriage, a teacher at a school in Kirkstall, near Leeds, and he had distant relatives in Wharefedale who were tenant farmers of Lord Harwood and lived in a delightful old farmhouse, dating from 1577, called The Nunnery at Arthington. He often used to walk to or from Arthington on Sundays and 'get a good lunch'.

At Leeds with Ingold, Charles continued the work, commenced with Thorpe, on tautomerism and reaction mechanism, but he never became involved in the Ingold-Robinson controversy on aromatic nitration. He played soccer for the University of Leeds and in 1926 his team won the Christie Cup in competition with the Universities of Manchester and Liverpool for the first time in 15 years; he was elected captain in 1928. He played twice for the combined Northern Universities XI before the International Selection Committee, but to his disappointment never secured an England cap. Leeds was an excellent centre for music and he had the good fortune to hear performances by Rosenthal, Hoffmann, Backhaus, Rubinstein, Moiseiwitch, Brailowsky, Cortot, Solomon, Smeterlin, Rachmaninov, Curzon and Paderewski (who at the time was Prime Minister of Poland). In 1926 he was awarded a Senior Research Studentship of the Royal Commission for the Exhibition of 1851 and for a variety of reasons decided to hold the award at Leeds instead of going to Europe. In the summer of 1929, he became a demonstrator in Organic Chemistry at Leeds, and on the strength of this appointment married Eileen West on 18 July 1929. Eileen was later found to be a distant cousin of Margery Bell (née West), the wife of the eminent physical chemist, R.P. Bell, FRS. Eileen Shoppee was from Leeds and was in her youth a fine tennis player – of Yorkshire County standing – while Charles himself was still playing competitive tennis in the Langland tournament in Swansea two decades later.

In 1930, Ingold left Leeds for University College London, and Shoppee, as well as several other students were left (in their words) 'high and dry' in the provinces. He obtained the DSc degree (London) in 1931, and was promoted to Assistant Lecturer in 1936. He made several attempts to move from Leeds during the period 1931-1938, but junior academic posts were in short supply following the financial crisis of 1930 and the subsequent depression. On a visit to the University of Manchester, he had the good fortune to meet I.M. Heilbron, FRS, and told him that he was stranded in Leeds. On Heilbron's advice, he persuaded the University of Leeds to nominate him for a Rockefeller Research Fellowship in 1938. In the Spring of 1939, on the very same day, he received two letters: one offering him a Leverhulme Research Fellowship at the University of Oxford for two years, the other offering him a Rockefeller Research Fellowship for one year at any university that he cared to select. Eventually he decided, with some heartache, to accept the Rockefeller invitation, and then there arose the question of where to go. He decided against Harvard or Yale as perhaps being too much like England and was tempted to go to Butenandt at the Kaiser Wilhelm Institut in Berlin, but his wife considered it would be too dangerous. He then thought of going to L. Ruzicka in Zurich and sought the advice of Heilbron, who pointed out that Ruzicka had a very large research group and that Shoppee would see little or nothing of the great man, whereas Reichstein had left Zurich in 1938 for Basel and had a relatively small research group. So Charles, with his wife and six-year-old daughter, proceeded to Basel. The move was to shape his science for the future as he combined his Ingoldian heritage of mechanistic organic chemistry with his freshly acquired skills in steroid chemistry to excellent effect.

Basel 1938-1945 and London 1945-1948

On 3 September 1939 Charles listened with dismay, but without surprise, to Neville Chamberlain's broadcast declaring war on Germany and at once wrote to the Vice-Chancellor of the University of Leeds offering to resign his Research Fellowship and return home; but he was instructed to continue his work, unless he received other instructions from the British Consulate-General in Basel. During the winter of 1939 and the spring of 1940 he worked with Reichstein on the structures of the adreno-cortical steroid hormones and completed some of his best experimental work. He acquired Reichstein's micro-technique and learnt how to do column chromatography with colourless, non-fluorescent compounds. At Whitsuntide in 1940, with war news getting worse and worse, the family attempted to return to England, but their French visas never came through, and they were compelled to remain in the 'largest and most beautiful concentration camp in Europe', viz Switzerland, for six years. His contribution to the war effect was accordingly confined to collecting news about Germany, and to 'gathering' specimens of petrol from German lorries in Basel and analysing the samples.

In 1944, Charles was appointed, in absentia, through the good offices of Sir Ian Heilbron to a Readership in Chemistry in the University of London, tenable at the Royal Cancer Hospital (now the Royal Marsden Hospital). After a nightmarish journey from Basel to London, taking three days and zigzagging across the Channel in a very small steamer 'The Isle of Thane', he took up his Readership in May 1945 and the family was able to celebrate VE Day in London. At the Royal Cancer Hospital, he worked on the steroid constituents of the unsaponifiable extract of human Bantu livers, but could isolate only cholesterol and its oxidation and dehydration products.

Swansea 1948-1956

In 1948, Shoppee was appointed to the Chair of Chemistry in the University of Wales at the University College, Swansea, succeeding J.E. Coates, a physical chemist. He continued the application of reaction mechanism to the determination of configuration of steroids with some success, and was elected to the Royal Society of London in 1956. By present standards, the 1948 Swansea Department of Chemistry would be regarded as far too small a department to give an adequate training in chemistry or opportunities for research. Charles had five members of staff together with a full time demonstrator. (Three of the five subsequently became professors and the demonstrator founded a special chemicals company.) In his eight years in Swansea the department produced about 130 Honours graduates in chemistry and from these a vigorous research school developed. Current orthodoxy suggests that the number of postgraduates would be inadequate for a viable research training, but such a view is hardly tenable, given that the Swansea department produced six professors (R.J.W. Cremlyn, W.O. George, D.H. Richards, M.W. Roberts, J.M. Thomas, W.J. Thomas), plus a polytechnic director (D.W.F. James) and a number of university readers and senior lecturers. Shoppee was able to generate enthusiasm amongst his staff and students. He had a genial, friendly disposition and was ready to ask his most junior colleagues for their advice on research problems. In the teaching of chemistry he had a favourite adage, 'there are not three chemistries, organic, inorganic and physical, but just one – chemistry itself'. He consequently supported the research interests of all his colleagues with students and finance for apparatus and expensive chemicals, despite the fact that the departmental funding was generally hard-pressed. He was also ready to listen to the beginning research students and to accept their choice of research topic and supervisor, even when this did not coincide with his own inclinations. He was often accompanied by his dog, Wally, and a member of the technical staff would be requested to exercise the dog in the adjacent park. It was not uncommon to see Shoppee returning to his home for lunch as a pillion rider on a motorcycle driven by a member of the technical staff, with the dog occupying an intermediate position.

Sydney 1956-1969

However, the damp climate of Wales affected Eileen Shoppee's health and, after she had suffered a long series of upper respiratory tract ailments, Charles was advised by former colleagues in Harley Street to seek a warmer and sunnier climate for her. He therefore accepted an invitation to the Chair of Organic Chemistry at the University of Sydney at the end of 1956, following the resignation of Arthur Birch who left Sydney for Manchester. When his emigration to Australia became known, Shoppee was jokingly asked, in view of his stereo chemical interests, whether going 'down-under' would entail an inversion of nomenclature. After some pondering he realised that it was the subject of a joke. The Sydney sunshine restored his wife's health and they began to enjoy the beauties of a 'new and fascinating continent'.

The early part of Shoppee's tenure at Sydney coincided with the relocation of the School of Chemistry from its rather ramshackle accommodation in the Science Road of the University to the modern building in Western Avenue where it remains to this day. More importantly, his tenure coincided with the period of expansion and flowering of Australian universities to which he made major contributions. Shoppee continued to apply reaction mechanistic concepts and new techniques to structure determination in natural products, mainly within the context of steroid chemistry, a major part of the work being pursued in collaboration with Associate Professor Ruth E. Lack. Shoppee was elected a Fellow of the Australian Academy of Science in 1958, and served as a member of Council 1959-62 and Vice President, 1961-62. While Shoppee never sought administrative positions within the University of Sydney, he was throughout his tenure the head of the Department of Organic Chemistry by virtue of his appointment as Professor, and he worked conscientiously and successfully on behalf of his Department with the invaluable help of Ern Ritchie, FAA, who was to succeed him as Professor of Organic Chemistry in 1969. Shoppee also served a period as Dean of the Faculty of Science (1966-7) and, while this position was far less central than it is at present, he rendered distinguished service to the Faculty in this capacity. He benefited from the former isolation of Australia that had made sabbatical leave much more accessible than in the UK. Thus, he was able to visit the US and the UK every two years. These periods of leave proved extremely stimulating, and in 1967-8 he learnt about the Woodward-Hoffman Rules, and recognised that some of his early work with Ingold at Leeds in 1928 had involved the thermal ground-state cycloaddition of a pentadienyl cation. A paper to this effect appeared in 1969, the year of his retirement, thereby closing the circle on a remarkable career.

Post-'retirement' 1970-1994

He was compulsorily retired at the age of 65 after a year rendered very difficult by the need to become acting head of the School of Chemistry as a consequence of the illness of his senior professorial colleague, R.J.W. Le Fèvre, FRS, and the subsequent illness and death of his junior professorial colleague, A.E. Alexander, FAA. However, associates in the USA had heard that he would be available in 1970, and he was offered the Foundation Welch Professorship of Chemistry at Texas Technological University (Lubbock, Texas), which he took up in January 1970 for a period of five years. He continued some steroid work, but concentrated the main effort of his group on the cycloadditions of penta-1,4-dienyl cations. He retired from the Welch Chair in 1975, and he and his wife returned to Australia to be closer to their daughter, Adrienne Horrigan, her husband William, and their four grandchildren. After a period as an honorary professorial fellow at Macquarie University (1976-9) Charles moved to Melbourne to be closer to his family, following the death of his beloved Eileen. He was appointed an honorary visiting professor at La Trobe University in 1980 and maintained his research interests into his middle eighties, working at the bench for one day each week up until the age of 87. In his letters he noted that the University encouraged him to 'waste their money on his chemicals' so that he could pursue some longstanding interests.

Scientific work

Prewar period (1921-1939)

After Shoppee graduated from the University of London, he was invited by Christopher Ingold, the doyen of UK physical-organic chemists to join him at the University of Leeds where he had just accepted a chair in chemistry. Ingold's influence on the whole of organic chemistry was enormous and clearly left its mark on Shoppee. Although Shoppee was to devote most of his future research to the chemistry of steroids, the emphasis was very much on mechanism and more physical aspects: inter alia, he published a series of 70 papers on 'Steroids and Walden Inversion' (see below). Late in his career, he was to become ever more preoccupied with structure and mechanism. At Leeds he continued the work, commenced with Thorpe, on tautomerism and reaction mechanisms until Ingold's departure back to London. Later, during the period 1931-8, he extended these studies to various cyclopentenes, publishing a series of papers jointly with Harold Burton.

Basel (1939-1945)

Supported by a Rockefeller Research Fellowship, Shoppee decided to join Tadeus Reichstein's group at Basel in the spring of 1939, a fateful decision in several respects. The adrenal glands of mammals comprise two sharply differentiated regions, the medulla producing (-)-adrenaline, and the cortex elaborating several hormones essential to life. Absence of these hormones, following destruction of the glands by tubercular infection (Addison's disease), or bilateral adrenalectomy, was shown to lead to multiple insufficiency symptoms and death. About 1930, adrenocortical extracts were prepared, which by daily injection were capable of maintaining patients with Addison's disease and adrenalectomized animals alive for practically unlimited periods. It was at first thought that the biological activity of such extracts was due to a single substance, but during the period 1935-60 forty-seven compounds were isolated. Eight of these compounds are highly active, including cortexone, aldosterone, cortisone and cortisol, this last substance being the most important adreno-cortical hormone. Four groups of workers were engaged in the isolation of individual compounds, thirty one of which were discovered by the Reichstein group. Milligram amounts of individual steroids were isolated from half a tonne of adrenal glands that had been obtained from 20,000 cattle. Shoppee discovered that the inert 11-oxygen function, characteristic of the adrenocorticoids, could be smoothly removed as an axial 11b-hydroxyl group by acid catalysed dehydration. Subsequent conversion into known steroids provided the first direct structural correlation for these compounds.

Reichstein and Shoppee also worked on the structures of cardiotonic glycosides and their aglycones. Certain steroidal glycosides isolated from plants possess powerful cardiotonic activity. Acidic or enzymatic hydrolysis affords the steroid aglycones or 'genins'. The cardiotonic property is associated with the special structure of the aglycone but is modified in regard to solubility and transport by the nature of the conjugated sugars. Use of digitalis in heart therapy was introduced in 1785 by the Scottish physician William Withering and met with spectacular success. Administration in cases of impaired heart function leads to decreased rate and increased intensity of the heart beat, while over-dosage produces systolic stoppage of the heart. In addition to use in cardiotherapy, some glycosides have been used as drugs in 'trials by ordeal' and as arrow poisons. The free aglycones are convulsive poisons rather than heart stimulants and are of little medicinal value. The main sources of the glycosides are plants of the Apoeynaceae, Liliaceae, Ranunculaceae, and Scrophulariaceae; certain genera of Digitalis (foxglove) furnish most of the drugs of therapeutic value.

Figure 1. Molecular structures for the sapogenin diginigenin.

Shoppee and Reichstein worked on the structure of diginin, isolated from leaves of Digitalis purpurea by Karrer in 1936, which was actually devoid of cardiac activity; 13 g of glycoside was supplied by Hoffmann LaRoche. By a series of transformations including Wolff-Kishner reduction and hydrogenation, Shoppee was able to degrade the derived aglycone, diginigenin, to the parent hydrocarbon, which was not identical with any hydrocarbon known at the time, and arrived at the tentative formula (1). An intermediate diketone was later identified by Press and Reichstein by synthesis as 5a,14b,17a-pregnane-3,20-dione. This evidence established the steroid nature of diginigenin and the location of oxygen functions at C3 and C20. It was another two decades, however, before Shoppee, in collaboration with Ruth Lack and Alex Robertson at the University of Sydney, established the correct structure as (2) with the benefit of NMR data. In 1943, with Reichstein's approval, Shoppee commenced to apply reaction mechanistic concepts to the reactions of natural products, particularly steroids where he was in the vanguard of a huge and widespread activity prompted in part by the pharmaceutical industry's interests in these important compounds.

Post-war period (1945-1948)

In May, 1945 Shoppee took up a Readership in Chemistry in the University of London and was based at the Royal Cancer Hospital. While there, he initiated his remarkable series of 70 papers on 'Steroids and the Walden Inversion', the latter term describing a process (which would now be labelled as SN2 substitution – cf. Fig. 2) whereby a group attached to an organic molecule is replaced by another group with inversion of the configuration of the carbon atom bearing the leaving group.

Figure 2. The Walden inversion.

In practice, the title of the series was a convenient label for wide-ranging explorations of structure, stereochemistry and mechanism. Ironically, much of the chemistry described in the very first paper involved retention of configuration rather than inversion. At the time there was considerable controversy over the conformation (shape) of the 6-membered cyclohexane ring and compounds containing this structure. Two major conformations are possible (Fig. 3). One is a rigid puckered shape described as a chair in which carbons 2,3 and 5,6 are coplanar, with C-1 above this plane and C-4 below. The second conformation is quite mobile and has C-1 and C-4 both above the plane and is described as a boat. Shoppee calculated that the barrier between the two conformations should be c.10 kcal mmol-1, a remarkably close estimate to the now established value of 11 kcal mmol-1. Sir Derek Barton (with whom Shoppee later published a brief communication on the conformation of cyclohexene) received the Nobel Prize for his research in this area.

Figure 3. Chair and boat conformations for cyclohexane.

Swansea (1948-1956)

Shoppee was invited to the Chair of Chemistry in this small but vigorous department. However, as in much of the UK, not much research had been done during the war and its aftermath. He set about building it up and was to enhance its standing considerably. He continued his research on steroids, a significant part of it in collaboration with G.H.R. Summers, publishing prolifically on transformations applied to various parts of these molecules. In addition to continuing the 'Walden inversion' series, he also began in 1952 a new series of (ultimately) 39 papers on broader aspects of steroid chemistry. One special interest was the behaviour of D5-3b-hydroxy steroids (a major feature of cholesterol). From his earlier work at Leeds with Ingold, Shoppee recognised that in substitution reactions at C-3, the D5-ene bond was participating in the reaction (partial bonding between C-3 and C-5) so that retention rather than the more normal inversion prevailed. Under the right conditions, a bond is actually formed between C-3 and C-5 with addition of a ligand to C-6 to form an 'i-steroid' (Fig. 4).

Figure 4. Mechanism for the formation of i-steroids.

Again, we should note that although such changes would be obvious with the benefit of modern spectroscopic techniques, it was a triumph of analytical reasoning to deduce such changes in their absence. And while the results from these and other studies pursued by Shoppee and his co-workers were of vital importance to our knowledge of steroid chemistry, they also informed wider areas of endeavour in our understanding of modern organic chemistry. During this period, he published more than 65 articles and original papers, the value of which was recognised in 1956 by his election to the Royal Society of London.

University of Sydney (1956-1969)

Arriving in Sydney must have been a terrible shock for Shoppee. It was prior to the Murray Report in 1957 that was to revolutionise the funding and organisation of Australian universities under Commonwealth auspices (with enormous resistance from the States). Research funding and modern equipment for organic chemists were almost non-existent; there was not even an infra-red spectrometer in the organic department, while it was necessary to plot ultra-violet spectra by hand. Shoppee's predecessor, Arthur Birch, had departed for a chair at Manchester in sheer frustration, prompting newspaper headlines referring to 'Beggars in Mortarboards'. David Craig and Ronald Nyholm left soon afterwards, reinforcing the message, although Birch and Craig were to return in 1967 to found the Research School of Chemistry at the Australian National University; Nyholm participated in the planning, but elected to remain in the UK.

Nevertheless, Shoppee's research on steroids prospered. He continued his interests in the bromination of steroidal ketones, but branched out to modification of various steroidal skeletons and the insertion of nitrogen into various rings in a search for interesting biological activity. His research was given a considerable boost with the arrival of modern spectrometric methods (for organic chemists) and he embraced with enthusiasm these new techniques, especially NMR spectroscopy and mass spectrometry (in addition to ultra-violet and infra-red spectroscopy that had finally been established at Sydney). The techniques were liberating and, inter alia, Shoppee revisited long-standing problems, finally deriving definitive structures for several steroidal sapogenins, including diginigenin (see above), digifologenin and digacetigenin. With the publication of the 'Woodward-Hoffman Rules' in 1964, the principles underlying huge tracts of hitherto poorly understood organic mechanisms were revealed. For Shoppee, it was intoxicating and he revisited the research that had been undertaken with Ingold and then Burton, finally achieving a full understanding of the processes involved.

Texas Technological University (1970-1974)

Following his retirement from Sydney University, Shoppee moved to a chair at 'Texas Tech' where he continued his interests in electrocyclic processes, publishing a dozen or so papers in this area. He was especially interested in re-examining the thermal ground-state [p2s + p2a] conrotatory cycloadditions of penta-1,4-dienyl cations, the photochemical excited-state [p2s + w2s + p2s] disrotatory cycloaddition of a penta-1,4-dienide anion, and some photochemical excited-stated [p2s + p2s] or [p2a + p2a] disrotatory cycloadditions of penta-1,4-diene molecules.

'Retirement' years (1975-1994)

Shoppee returned to Australia in August 1975 and took up an appointment as an honorary professorial fellow at Macquarie University (1976-1979) and then moved to Melbourne to be closer to family, following the death of his wife. Shoppee was appointed honorary visiting professor at La Trobe University in 1980 and maintained a vigorous interest in chemistry until his death on 20 October 1994, aged 90. As a measure of his fascination with chemistry, he was still working at the bench at the age of 87.

Conclusion

We should place Shoppee's scientific achievements into context. Contemporary organic chemists enjoy the enormous benefits of spectroscopic techniques and separation methods that only became available towards the end of Shoppee's career. Without these aids most modern practitioners would not know where to begin, and yet it was a field in which he excelled, especially the assignment of stereochemistry. Problems that could now be solved in a few minutes by a first-year undergraduate using nuclear magnetic resonance (NMR) spectroscopy, would have taken Shoppee and his colleagues several months, or even longer. The availability of reagents was extremely limited and very few were commercially available. From a modern perspective, it is difficult to understand how it was possible to isolate and deduce structures of organic molecules, especially those as complex as the adrenocortical steroid hormones, before the availability of NMR spectroscopy in the late 1950s. And yet chemical and some limited physical methods were sufficient for Shoppee and his co-workers until the arrival of the first NMR spectrometer (a Varian A60) at Sydney in 1962. The advent was almost too late for Shoppee, but it was a turning point for those of us that followed. In 1998, the University of Wales at Swansea launched the 'C.W. Shoppee Memorial' appeal to fund scholarships for entering chemistry students. Students from all over the world are eligible, reflecting the international nature of the career pursued by Shoppee.

About this memoir

This memoir was originally published in Historical Records of Australian Science, vol.14, no.4, 2003. It was written by Professor Lewis N. Mander, Research School of Chemistry, Australian National University, Canberra, Australia.

Acknowledgments

I am most grateful to William Horrigan, the late Sir Ewart Jones, Brian Gowenlock, John Davies and R.H. Davies for providing material relating to the earlier stages of Shoppee's career, and to Sever Sternhell and Henry Shine for information on the later years.

Bibliography

  1. Ingold, C.K., Shoppee, C.Wm., Thorpe, J.F. Mechanism of tautomeric interchange and the effect of structure on mobility and equilibrium. I. The three-carbon system. J. Chem. Soc. (1926), pp. 1477-1488.
  2. Ingold, C.K., Shoppee, C.W. Constitution of the yellow sodium compounds formed from ethyl citraconate (or itaconate) and ethyl sodiomalonate. J. Chem. Soc. (1926), pp. 1912-1917.
  3. Rothstein, Eugene, Shoppee, C.W. Ring-chain tautomerism. XV. The hydroxy-lactone type. J. Chem. Soc. (1927), pp. 531-534.
  4. Shoppee, Charles Wm. Mobile hydrogen tautomerism analogous to the Wagner-Meerwein rearrangement. II. The tautomerism of 1 (or 5)-hydroxy-2,2,3,3-tetramethylcyclopentan-5(or 1)-one and its derivatives. J. Chem. Soc. (1928), pp. 1662-1670.
  5. Ingold, Christopher K., Shoppee, Charles Wm. Possibility of ring-chain valency tautomerism and of a type of mobile-hydrogen tautomerism analogous to the Wagner-Meerwein rearrangement. III. Orientation of some cyclic derivatives of phorone. J. Chem. Soc. (1928), pp. 1868-1873.
  6. Shoppee, Charles Wm. Possibility of ring-chain valency tautomerism and of a type of mobile-hydrogen tautomerism analogous to the Wagner-Meerwein rearrangement. IV. Substitution reactions of some cyclic derivatives of phorone. J. Chem. Soc. (1928), pp. 2360-2365.
  7. Shoppee, Charles Wm. Mobility of symmetrical triad(prototropic) systems. III. Three-carbon prototropy in an a,g-diphenylallyl ether. J. Chem. Soc. (1928), pp. 2567-2571.
  8. Shoppee, C.W. Possibility of ring-chain valency tautomerism and of a type of mobile-hydrogen tautomerism analogous to the Wagner-Meerwein rearrangement. V. Pinacolic electron displacement as an explanation of various intramolecular transformations. Proc. Leeds Phil. Lit. Soc., Sci. Sect. 1(Pt. VII) (1928), pp. 301-311.
  9. Ingold, Christopher K., Shoppee, Charles Wm. Mobility of symmetrical triad (prototropic) systems. IV. Mobility in the simple three-carbon system terminated by aryl groups. J. Chem. Soc. (1929), pp. 447-455.
  10. Ingold, Christopher Kelk, Shoppee, Charles Wm. Mobility of symmetrical triad prototropic systems. V. A new triad system (methyleneazomethine). J. Chem. Soc. (1929), pp. 1199-1204.
  11. Shoppee, C.W., Simonsen, J.L. Norpinic acid. Chemistry and Industry, 7 (1929), pp. 730-731.
  12. Shoppee, Charles Wm. Symmetrical triad prototropic systems, VI. The effect of substitution on tautomeric mobility and equilibrium in the a,g-diphenylpropene system. J. Chem. Soc. (1930), pp. 968-985.
  13. Ingold, Christopher Kelk, Shoppee, Charles Wm. Spatial configuration of the simple valencies of allene. J. Chem. Soc. (1930), pp. 1619-1622.
  14. Shoppee, Charles Wm. Symmetrical triad prototropic systems. VII. The analogy between symmetrical triad systems and aromatic side-chain reactivity and the effect of p-substitution on mobility and equilibrium in the g-diphenylmethyleneazomethine system. J. Chem. Soc. (1931), pp. 1225-1240.
  15. Shoppee, Charles Wm. Symmetrical triad prototropic systems. VIII. Analogy between symmetrical triad systems and aromatic side-chain reactivity and the effect of m-substitution on mobility and equilibrium in the a,g-diphenylmethyleneazomethine system. J. Chem. Soc. (1932), pp. 696-711.
  16. Shoppee, Charles W. Symmetrical triad prototropic systems. IX. The influence of polynuclear aryl groups upon mobility and equilibrium in the a,g-diarylmethyleneazomethine system. J. Chem. Soc. (1933), pp. 37-45.
  17. Burton, H., Shoppee, C.W. Anionotropic and prototropic changes in 4-hydroxycyclo-pentenones. Chemistry and Industry 10 (1932), p. 981.
  18. Burton, Harold, Shoppee, Charles W., Wilson, Christopher L. Anionotropic and prototropic changes in cyclic systems. I. Hydroxycyclopentenones. J. Chem. Soc. (1933), pp. 720-731.
  19. Shoppee, Charles W. Effect of nuclear halogen substitution on triad prototropic systems in relation to aromatic side-chain reactions. J. Chem. Soc. (1933), pp. 1117-1120.
  20. Burton, Harold, Shoppee, Charles W. Anionotropic and prototropic changes in cyclic systems. II. The hydroxy-3,4-diphenyl-5-benzylidenecyclopentenones. J. Chem. Soc. (1934), pp. 197-201.
  21. Burton, Harold, Shoppee, Charles W. Anionotropic and prototropic changes in cyclic systems. III. The isomeric chloro-3,4-diphenylcyclopentenones. J. Chem. Soc. (1934), pp. 201-205.
  22. Burton, Harold, Shoppee, Charles W. Anionotropic and prototropic changes in cyclic systems. IV. Anionotropic and prototropic changes in cyclic systems. Hydroxy-3,4-diphenyl-5-isopropylidenecyclopentenones. J. Chem. Soc. (1934), pp. 205-207.
  23. Burton, Harold, Shoppee, Charles W. Anionotropic and prototropic changes in cyclic systems. V. The system derived from 1-hydroxyindene. J. Chem. Soc. (1935), pp. 1156-1161.
  24. Ingold, Christopher K., Parekh, Mukundrai M., Shoppee, Charles W. Possibility of ring-chain mesomerism. II. Properties of ADa,e-hexadiene-a,a,g,g,d,d,z,z-octacarboxylic esters. J. Chem. Soc. (1936), pp. 142-153.
  25. Shoppee, Charles W. 1,2,3-Triketotetramethylcyclopentane: a blue triketone. J. Chem. Soc. (1936), pp. 269-274.
  26. Shoppee, Charles W. s-Di-p-anisylpinacol. J. Chem. Soc. (1936), pp. 506-507.
  27. Burton, Harold, Shoppee, Charles W. Anionotropic and prototropic changes in cyclic systems. VI. cis-and trans-3,4-Diphenylcyclopentanones. The structure of the ketone obtained by reduction of 2-hydroxy-3,4-diphenyl-D2-cyclopentenone with hydriodic acid. J. Chem. Soc. (1939), pp. 567-573.
  28. Burton, Harold, Shoppee, Charles W. Anionotropic and prototropic changes in cyclic systems. VII. The structure of the chlorodiphenylcyclopentenone obtained by the action of hydrogen chloride on anhydroacetonebenzil. J. Chem. Soc. (1939), pp. 1408-1415.
  29. Shoppee, C.W., Reichstein, T. Constituents of the adrenal cortex and related compounds. XXXVIII. Conversion of substance A into substance N. Helv. Chim. Acta, 23 (1940), pp. 729-739.
  30. Shoppee, C.W. Constituents of the adrenal cortex and related compounds. XXXIX. Chemical proof for the presence of the oxygen atom in the 3-position. Helv. Chim. Acta, 23 (1940), pp. 740-746.
  31. Shoppee, C.W., Reichstein, T. Diginin. I. Helv. Chim. Acta, 23 (1940), pp. 975-991.
  32. Shoppee, C.W. Constituents of the adrenal cortex and related substances. XL. 17-Isodesoxycorticosterone. Helv. Chim. Acta, 23 (1940), pp. 925-934.
  33. Shoppee, C.W., Reichstein, T. Constituents of the adrenal cortex and related substances. XLIV. 11-Dehydroprogesterone. Helv. Chim. Acta, 24 (1941), pp. 351-360.
  34. Shoppee, C.W., Reichstein, T. Constituents of the adrenal cortex and related substances. XLVIII. Partial synthesis of substance L. Helv. Chim. Acta, 24 (1941) pp. 418-420.
  35. Shoppee, C.W. The chemistry of the steroids. Ann. Rev. Biochem. 11 (1942), pp. 103-150.
  36. Shoppee, C.W., Reichstein, T. Diginin. II. Constitution of diginose. Helv. Chim. Acta, 25 (1942), pp. 1611-1123.
  37. Shoppee, C.W., Prins, D.A. Constituents of the adrenal cortex and related substances. LVII. 17-Hydroxy-20-keto steroids and the mechanism of their rearrangement to polyhydrochrysene derivatives. Helv. Chim. Acta, 26 (1943), pp. 185-200.
  38. Shoppee, C.W., Prins, D.A. Constituents of the adrenal cortex and related substances. LVIII. Rearrangement of 17-hydroxy-20-keto steroids into polyhydrochrysene derivatives. Acetylation in the presence of boron fluoride. Helv. Chim. Acta, 26 (1943) pp. 201-223.
  39. Shoppee, C.W., Prins, D.A. Rearrangement of 17-hydroxy-20-keto steroids. III. Helv. Chim. Acta, 26 (1943), pp. 1004-1016.
  40. Shoppee, C.W., Reichstein, T. Constituents of the adrenal cortex and related substances. LXIII. 11-Epicorticosterone acetate and two isomeric anhydrocorticosterone acetates. Helv. Chim. Acta, 26 (1943), pp. 1316-1328.
  41. Shoppee, C.W., Prins, D.A. Rearrangement of 17-hydroxy 20-keto steroids. IV. Treatment of 3(b),17(a)-diacetoxy-20-allopregnanone with MeMgBr. Helv. Chim. Acta, 26 (1943), pp. 2089-2095.
  42. Shoppee, C.W. Rearrangement of 17-hydroxy 20-keto steroids. V. 17a-Methyl-D-homoetiocholane and some derivatives. Helv. Chim. Acta, 27 (1944), pp. 8-23.
  43. Shoppee, C.W. Diginin. III. Degradation of diginigenin to a hydrocarbon, diginane, C21H36. Helv. Chim. Acta, 27 (1944), pp. 246-260.
  44. Shoppee, C.W. Diginin. IV. Diginin and diginigenin. Helv. Chim. Acta, 27 (1944), pp. 426-435.
  45. Shoppee, C.W. Structure of adrenocortical metabolites: D9,11-Androstene-3,17-dione. J. Chem. Soc. (1946), pp. 1134-1137.
  46. Shoppee, C.W. Steroids and the Walden inversion. I. Derivatives of androstane and cholestane. J. Chem. Soc. (1946), pp. 1138-1147.
  47. Shoppee, C.W. Steroids and the Walden inversion. II. Derivatives of D5-cholestene and D5-androstene. J. Chem. Soc. (1946), pp. 1147-1151.
  48. Shoppee, C.W. The configuration of desoxycholic acid. Chemistry and Industry (1947), pp. 109-112.
  49. Shoppee, C.W. 9-Androstene-3,17-dione. Remarks on the 9-androsten-3(b)-ol-17-one of H. Reich and A. Lardon. Helv. Chim. Acta, 30 (1947), pp. 766-768.
  50. Shoppee, C.W. C/D-ring union in the estrogenic hormones. Nature, 160 (1947), pp. 64-66.
  51. Shoppee, C.W. Nature of C/D-ring union in the estrogenic hormones. Nature, 161 (1948), p. 207.
  52. Shoppee, C.W. Steroids and related compounds. Ann. Repts Progress Chem. (Chem. Soc. London), 43 (1946), pp. 200-231.
  53. Boyland, E., Shoppee, C.W. Metabolism of polycyclic compounds: the configuration of the dihydroxydihydroanthracenes produced from anthracene. J. Chem. Soc. (1947), pp. 801-804.
  54. Shoppee, C.W. Steroids and related compounds. Ann. Repts Progress Chem. (Chem. Soc., London), 44 (1947), pp. 170-216.
  55. Shoppee, C.W. Steroids and the Walden inversion. III. Derivatives of 6-ketocholestane; direct proof of the stereochemical orientation of the hydroxy group in cholesterol. J. Chem. Soc. (1948), pp. 1032-1043.
  56. Shoppee, C.W. Steroids and the Walden inversion. IV. Derivatives of 6-ketositostane and 6,17-diketoandrostane. J. Chem. Soc. (1948), pp. 1043-1045.
  57. Boscott, R.J., Mandl, Anita M., Danielli, J.F., Shoppee, C.W. Cytochemical demonstration of ketosteroids. Nature, 162 (1948), p. 572.
  58. Shoppee, C.W. The Sommelet reaction. Nature, 162 (1948), pp. 619-620.
  59. Shoppee, C.W. Serini reaction. Experientia, 4 (1948), pp. 418-420.
  60. Shoppee, C.W., Summers, G.H.R. Steroids and the Walden inversion. VI. Reduction of 5-cholesten-3-one with lithium aluminum hydride. J. Chem. Soc. (1950), pp. 687-689.
  61. Shoppee, C.W., Lewis, D.G., Elks, J. Testosterone. Proof of configuration at C17. Chemistry and Industry (1950), p. 454.
  62. Shoppee, C.W. Stereochemical course of reactions at steroid C17. Nature, 166 (1950), pp. 107-108.
  63. Shoppee, C.W. Steroid configuration. Vitamins and Hormones (Academic Press: New York, N.Y.), 8 (1950), pp. 255-308.
  64. Shoppee, C.W. 'a-' and 'b-' Dihydroequilenin; configuration at C17. Chemistry and Industry (1950), p. 810.
  65. Shoppee, C.W. The i-steroid rearrangement. Bull. Soc. Chim. France (1951), pp. C120-C124.
  66. Shoppee, C.W. Boat conformation of cyclohexane. Chemistry and Industry (1952), pp. 86-87.
  67. Shoppee, C.W., Summers, G.H.R. Steroids. I. New preparation of the cholesteryl halides. J. Chem. Soc. (1952), pp. 1786-1790.
  68. Shoppee, C.W., Summers, G.H.R. Steroids. II. The preparation of epicholesteryl chloride and bromide. J. Chem. Soc. (1952), pp. 1790-1795.
  69. Shoppee, C.W., Summers, G.H.R. Steroids. III. 3-Methyl-A-norcholest-3(5)-ene. J. Chem. Soc. (1952), pp. 2528-2530.
  70. Klyne, W., Shoppee, C.W. Urane derivatives as D-homosteroids. Chemistry and Industry (1952), pp. 470-471.
  71. Shoppee, C.W. Structure and shape of steroid molecules in relation to biological activity. 2nd Congr. intern. biochim., Chim. biol. VII, Symposium biochim. des steroides (Paris) (1952), pp. 5-12.
  72. Shoppee, C.W., Summers, G.H.R. Steroids and Walden inversion. VII. The stereo chemistry and the mechanism of the iso-steroid rearrangement. J. Chem. Soc. (1952), pp. 3361-3374.
  73. Shoppee, C.W., Summers, G.H.R. Steroids and Walden inversion. VIII. The epimeric 6-hydroxy-2,3-secocholestane-2,3-dicarboxylic acids. J. Chem. Soc. (1952), pp. 3374-3381.
  74. Shoppee, C.W. The chemistry of cortisone. Ann. Rev. Biochem. 22 (1953), pp. 261-298.
  75. Gough, N., Shoppee, C.W. D-homosteroids as potential carcinogens. Biochem. J. 54 (1953), pp. 630-632.
  76. Elks, J., Shoppee, C.W. Steroids and Walden inversion. IX. Epimerization at C-17. J. Chem. Soc. (1953), pp. 241-245.
  77. Shoppee, C.W. Some Aspects of Steroid Stereochemistry. (Notre Dame University Press: Indiana) (1953), 30 pp.
  78. Evans, D.D., Shoppee, C.W. Steroids. IV. Solvolysis of epicholesteryl p-toluene sulfonate and other steroid p-toluene sulfonates. J. Chem. Soc. (1953), pp. 540-547.
  79. Garmaise, D.L., Shoppee, C.W. Potential carcinogens. I. D6-Steroids. J. Chem. Soc. (1953), pp. 245-249.
  80. Cremlyn, R.J.W., Garmaise, D.L., Shoppee, C.W. Steroids and Walden inversion. X. The reconversion of D-homosteroids into steroids. J. Chem. Soc. (1953), pp. 1847-1852.
  81. Bridgewater, R.J., Shoppee, C.W. Steroids and Walden inversion. XI. Acetolysis of the coprostanyl halides. J. Chem. Soc. (1953), pp. 1709-1715.
  82. Shoppee, C.W. Saturated electrophilic rearrangements. Chemistry and Industry (1954), pp. 759-760.
  83. Casanova, R., Shoppee, C.W., Summers, G.H.R. Steroids. V. Partial synthesis of 9,11-anhydrocorticosterone acetate [21-acetoxy-4,9(11)-pregnadiene-3,20-dione]. J. Chem. Soc. (1953), pp. 2983-2992.
  84. Ruff, A., Shoppee, C.W., Summers, G.H.R. Steroids. VI. Partial synthesis of 9,11-dehydroprogesterone. J. Chem. Soc. (1953), pp. 3683-3690.
  85. Blears, J.G., Shoppee, C.W. 7,22-Ergostadiene-3b,5a,6b-triol (cerevisterol). Chemistry and Industry (1953), p. 947.
  86. Lewis, J.R., Shoppee, C.W. Catalytic hydrogenation of 3a-hydroxy D5-steroids and derivatives. Chemistry and Industry (1953), p. 897.
  87. Barton, D.H.R., Cookson, R.C., Klyne, W., Shoppee, C.W. The conformation of cyclohexene. Chemistry and Industry (1954), pp. 21-22.
  88. Fudge, A.J., Shoppee, C.W., Summers, G.H.R. Steroids. VII. 5-Hydroxy derivatives of cholestane. J. Chem. Soc. (1954), pp. 958-964.
  89. Shoppee, C.W., Stephenson, R.J. Configuration of Marker's cholesteryl-3-carboxylic acid. Chemistry and Industry (1954), pp. 278-279.
  90. Shoppee, C.W., Stephenson, R.J. The reduction of a p-toluenesulfonate with sodium borohydride. Chemistry and Industry (1954), p. 311.
  91. Shoppee, C.W., Stephenson, R.J. Steroids and Walden inversion. XII. The epimeric 3-cholesterylacetic and 3-cholestanylacetic acids. J. Chem. Soc. (1954), pp. 2230-2242.
  92. Roberts, G., Shoppee, C.W., Stephenson, R.J. Steroids and Walden inversion. XIII. The epimeric cholest-5-ene-3-carboxylic acids and the epimeric cholestane-3-carboxylic acids. J. Chem. Soc. (1954), pp. 2705-2715.
  93. Lewis, J.R., Shoppee, C.W. Catalytic hydrogenation of epicholesteryl chloride. Chemistry and Industry (1954), p. 933.
  94. Roberts, G., Shoppee, C.W., Stephenson, R.J. Steroids and Walden inversion. XIV. 5-Hydroxycholestane-3•-carboxylic acid and related compounds. J. Chem. Soc. (1954), pp. 3178-3183.
  95. Roberts, G., Shoppee, C.W. Steroids and Walden inversion. XV. Mechanism and stereochemical course of Grignard carboxylations and oxygenations. J. Chem. Soc. (1954), pp. 3418-3422.
  96. Cremlyn, R.J.W., Shoppee, C.W. Steroids and Walden inversion. XVI. Epimeric cholestan-7-ols. J. Chem. Soc. (1954), pp. 3515-3518.
  97. Rees, R.W., Shoppee, C.W. Steroids. VIII. 3,5-Cycloergosta-7,9(11),22-trien-6b-ol (i-dehydroergosterol). J. Chem. Soc. (1954), pp. 3422-3428.
  98. Evans, D.D., Shoppee, C.W., Summers, G.R.H. Reduction of steroid ketoximes. Chemistry and Industry (1954), pp. 1535-1536.
  99. Cremlyn, R.J.W., Rees, R.W., Shoppee, C.W. Steroids and Walden inversion. XVII. Configuration of y-cholesterol and the attempted preparation of 4b-methoxy-5,7-cyclocholestane. J. Chem. Soc. (1954), pp. 3790-3794.
  100. Cremlyn, R.J.W., Shoppee, C.W. Steroids and Walden inversion. XVIII. The preparation and configuration of the epimeric 7-chlorocholestanes. J. Chem. Soc. (1954), pp. 3794-3797.
  101. James, D.R., Shoppee, C.W. Steroids and Walden inversion. XIX. The configurations of the bromination products of 6-oxocholestan-3b-yl acetate. J. Chem. Soc. (1954), pp. 4224-4227.
  102. Evans, D.E., de Paulet, A.C., Shoppee, C.W., Winternitz, F. Application of the Favorski reaction to steroid 3-ketones. Chemistry and Industry (1955), pp. 355-356.
  103. Lewis, J.R., Shoppee, C.W. Steroids. IX. Catalytic hydrogenation of 3a-substituted D5-steroids. J. Chem. Soc. (1955), pp. 1365-1370.
  104. James, D.R., Rees, R.W., Shoppee, C.W. Steroids. X. Preparation of unsaturated steroids. J. Chem. Soc. (1955), pp. 1370-1375.
  105. Davies, R.H., Meecham, Sylvia, Shoppee, C.W. Steroids and Walden inversion. XX. Kinetic study of the acetolysis of cholesteryl bromide. J. Chem. Soc. (1955), pp. 679-686.
  106. Shoppee, C.W., Williams, D.F. Steroids and Walden inversion. XXI. Kinetic study of the acetolysis of epicholesteryl bromide and p-toluene sulfonate. J. Chem. Soc. (1955), pp. 686-690.
  107. Pierce, J.H., Shoppee, C.W., Summers, G.H.R. Steroids and Walden inversion. XXII. The configuration of cholesterylamine. J. Chem. Soc. (1955), pp. 690-693.
  108. Pierce, J.H., Richards, H.C., Shoppee, C.W., Stephenson, R.J., Summers, G.H.R. Steroids and Walden inversion. XXIII. Production of 3a-substituted D5-steroids in replacement reactions of 3b-substituted D5-steroids. J. Chem. Soc. (1955), pp. 694-703.
  109. Lewis, J.R., Shoppee, C.W. Steroids and Walden inversion. XXIV. Methylation of 3-hydroxy steroids. J. Chem. Soc. (1955), pp. 1375-1378.
  110. Jones, D.N., Lewis, J.R., Shoppee, C.W., Summers, G.H.R. Steroids and Walden inversion. XXVI. 4b-Methoxycholest-5-ene, 6b-methoxycholest-4-ene, and related compounds. J. Chem. Soc. (1955), pp. 2876-2887.
  111. Barton, D.H.R., Page, J.E., Shoppee, C.W. Infrared absorption of halo steroids. J. Chem. Soc. (1956), pp. 331-336.
  112. Shoppee, C.W., Westcott, D.T. Steroids and Walden inversion. XXV. Kinetic study of the methanolysis of cholesteryl p-toluene sulfonate in the presence of methoxide ions. J. Chem. Soc. (1955), pp. 1891-1896.
  113. Lewis, H.R., Shoppee, C.W. Quinolizines and quinolizidines. I. Reduction of 4-oxoquinolizidines by LiAlH4. J. Chem. Soc. (1956), pp. 313-318.
  114. Shoppee, C.W. Configuration at C-22 of 20-isosapogenins. Chemistry and Industry (1956), pp. 467-468.
  115. Richards, H.C., Shoppee, C.W., Sly, J.C.P., Summers, G.H.R. Steroids and Walden inversion. XXVII. 3a-Cholesterylamine and 3a-coprostanylamine. J. Chem. Soc. (1956), pp. 1054-1059.
  116. James, D.R., Shoppee, C.W. Steroids and Walden inversion. XXVIII. Structure of the lactonic acid derived from 6a-hydroxy-2,3-secocholestane-2,3-dioic acid. J. Chem. Soc. (1956), pp. 1059-1064.
  117. James, D.R., Shoppee, C.W. Steroids and Walden inversion. XXIX. Configurations of the bromination products of 7-oxocholestan-3b-yl acetate. J. Chem. Soc. (1956), pp. 1064-1067.
  118. Shoppee, C.W., Evans, D.E., Richards, H.C., Summers, G.H.R. Steroids and Walden inversion. XXX. Epimeric coprostan-3-ylamines and cholest-4-en-3-ylamines. J. Chem. Soc. (1956), pp. 1649-1655.
  119. Shoppee, C.W., Summers, G.H.R., Williams, R.J.W. Steroids and Walden inversion. XXXI. Solvolysis of cholest-4-en-7b-yl (y-cholesteryl) p-toluene sulfonate. J. Chem. Soc. (1956), pp. 1893-1894.
  120. Shoppee, C.W., Williams, D.F. Steroids and Walden inversion. XXXII. 3,5-Cyclosteroid rearrangement. J. Chem. Soc. (1956), pp. 2488-2491.
  121. Shoppee, C.W., Bridgwater, R.J., Jones, D.N., Summers, G.H.R. Steroids and Walden inversion. XXXIII. Configuration of coprostanyl halides. J. Chem. Soc. (1956), pp. 2492-2499.
  122. Shoppee, C.W., Richards, H.C., Summers, G.H.R. Steroids and Walden inversion. XXXIV. Solvolysis of cholesteryl p-toluenesulfonate with thiophenoxide ions. J. Chem. Soc. (1956), pp. 4817-4821.
  123. Shoppee, C.W., Evans, D.E., Summers, G.H.R. Steroids and Walden inversion. XXXVI. Mechanism of deamination. J. Chem. Soc. (1957), pp. 97-103.
  124. Nes, W.R., Shoppee, C.W. Steroids. XI. 3,5-Cyclosteroid rearrangement of dehydro-ergosteryl p-toluenesulfonate. J. Chem. Soc. (1957), pp. 93-96.
  125. Evans, D.E., De Paulet, A.C., Shoppee, C.W., Winternitz, F. Steroids. XII. Examples of the Favorski.crn.i reaction. J. Chem. Soc. (1957), pp. 1451-1458.
  126. Shoppee, C.W., Agashe, B.D., Summers, G.H.R. Steroids. XIII. Catalytic hydrogenation of 3•-and 3b-substituted D4-steroids. J. Chem. Soc. (1957), pp. 3107-3112.
  127. Shoppee, C.W., Jones, D.N., Summers, G.H.R. Steroids and Walden inversion. XXXVII. Epimeric cholestane-2,3-diols. J. Chem. Soc. (1957), pp. 3100-3107.
  128. Shoppee, C.W., Cremlyn, R.J.W., Evans, D.E., Summers, G.H.R. Steroids and Walden inversion. XXXVIII. Deamination of epimeric cholestan-2-, -4-, and -7-ylamines. J. Chem. Soc. (1957), pp. 4364-4369.
  129. Shoppee, Charles W. Chemistry of the Steroids (Academic Press: New York) 1958, 314 pp.
  130. Shoppee, C.W., Summers, G.H.R. Steroids. XIV. Some 3b-fluoro steroids. J. Chem. Soc. (1957), pp. 4813-4816.
  131. Shoppee, C.W., Howden, M.E.H. 5a-Cholestan-6a-yl halides. Chemistry and Industry (London) (1958), pp. 414-415.
  132. Shoppee, C.W., Jenkins, R.H., Summers, G.H.R. Steroids and Walden inversion. XXXIX. Halogenation of 5a-cholestan-6-one and the pyrolysis of 5-chloro-5a-cholestan-6-one. J. Chem. Soc. (1958), pp. 1657-1663.
  133. Shoppee, C.W., Jenkins, R.H., Summers, G.H.R. Steroids and Walden Inversion. XL. Configurations of the bromination products of androstane-17-one. J. Chem. Soc. (1958), pp. 3048-3058.
  134. Shoppee, C.W., Sly, J.C.P. Aza steroids. I. 3-Aza-A-homo-5a-and 5b-cholestane. J. Chem. Soc. (1958), pp. 3458-3465.
  135. Shoppee, C.W., Sly, J.C.P. Steroids and Walden inversion. XLI. Deamination of some A-nor-, B-nor-, and 17-aminosteroids. J. Chem. Soc. (1959), pp. 345-356.
  136. Shoppee, C.W., Howden, M.E.H., Killick, R.W., Summers, G.H.R. Steroids and Walden inversion. XLII. 5•-Cholestan-4-one and some derivatives thereof. J. Chem. Soc. (1959), pp. 630-636.
  137. Shoppee, C.W., Rees, R.W., Summer, G.H.R., Phillips, G.D. Steroids and Walden inversion. XLIII. Bromination of 3,5-cyclosteroids. J. Chem. Soc. (1959), pp. 2786-2795.
  138. Young, W.G., Ireland, R.E., Wrigley, T.I., Shoppee, C.W., Agashe, B.D., Summers, G.H.R. Allylic rearrangements. XLII. Preparation and some reactions of 3b-chlorocholest-4-ene and 3a-chlorocholest-4ene. J. Am. Chem. Soc. 81 (1959) pp. 1452-1454.
  139. Shoppee, C.W., Connick, W., Davies, R.H. Steroids and Walden inversion. XLIV. Acetolysis of cholesteryl iodide. J. Chem. Soc. (1960), pp. 4857-4864.
  140. Shoppee, C.W., Lack, Ruth. Steroids and Walden inversion. XLV. 6b-Chloro-and 6b-bromo-5a-cholestane. J. Chem. Soc. (1960), pp. 4864-4873.
  141. Shoppee, C.W., Howden, M.E.H., Lack, Ruth. Steroids and Walden inversion. XLVI. 6a-Chloro-and 6a-bromo-5a-cholestane. J. Chem. Soc. (1960), pp. 4874-4879.
  142. Shoppee, C.W., Cymerman-Craig, J., Lack, Ruth E. Acetylenic compounds related to stilbestrol. III. Acetylenic alcohols derived from a-alkyldeoxyanisoins, and the a-alkyl-b-ethynylstilbenes. J. Chem. Soc. (1961), pp. 1311-1321.
  143. Shoppee, C.W., Roy, S.K., Goodrich, B. S. Steroids and Walden inversion. XLVII. 5a-Cholestan-1-one, A-nor-5a-cholestan-1-one, and some derivatives thereof. J. Chem. Soc. (1961), pp. 1583-1590.
  144. Shoppee, C.W., Johnston, G.A.R. Steroids and Walden inversion. XLVIII. Solvolysis of some 3-epimeric 4,4-dimethylsteroid p-toluenesulfonates. J. Chem. Soc. (1961), pp. 3261-3271.
  145. Shoppee, C.W., Lack, Ruth E. Steroids and Walden inversion. XLIX. Further observations on the bromination of 5b-cholestan-4-one. J. Chem. Soc. (1961), pp. 3271-3277.
  146. Shoppee, C.W., Krueger, G. Aza-steroids. II. 3-Aza-and 4-aza-A-homo-5a-and 5b-androstane, and the structure of neosaman. J. Chem. Soc. (1961), pp. 3641-3655.
  147. Shoppee, C.W., Craig, J. Cymerman, Lack, Ruth E. Acetylenic compounds related to stilbestrol. IV. The preparation of a-alkyl-b-ethynyl-4,4'-dihydroxystilbenes. J. Chem. Soc. (1961), pp. 2291-2298.
  148. Shoppee, C.W., Howden, M.E.H., Johnston, G.A.R. Constituents of the bark of Balanops australiana. J. Chem. Soc. (1962), pp. 498-501.
  149. Shoppee, C.W., Johnston, G.A.R. Steroids and Walden inversion. L. Comparative studies of •-bromo and a,a'-dibromo ketones derived from friedelin and from 5a-cholestan-6-one. J. Chem. Soc. (1962), pp. 1246-1254.
  150. Shoppee, C.W., Krueger, G., Mirrington, R. N. Aza steroids. HI. 3-Aza-A-homocholest-4a-and -5-ene and related compounds. (1962), J. Chem. Soc. pp. 1050-1055.
  151. Shoppee, C.W., Lack, Ruth E., Scott, Janice. Steroids. XV. Tribromination of 5a-cholestan-3-one. J. Chem. Soc. (1962), pp. 2233-2238.
  152. Shoppee, C.W., Johnston, G.A.R. Steroids and Walden inversion. LI. Solvolysis of 4,4-dimethylcholest-5-en-3a-yl p-toluenesulfonate. J. Chem. Soc. (1962), pp. 2684-2691.
  153. Shoppee, C.W., Killick, R.W., Krueger, G. Aza steroids. IV. 3-aza-5a-and -5b-cholestane, 4-aza-5aa-and -5b-cholestane, and related compounds. J. Chem. Soc. (1962), pp. 2275-2285.
  154. Shoppee, C.W., Johnston, G.A.R., Lack, Ruth E. Steroids. XVI. The bromination of some 3-oxo steroids methylated in ring A. J. Chem. Soc. (1962), pp. 3604-3610.
  155. Shoppee, C.W., Lack, Ruth E., Robertson, A.V. Steroids. XVII. The structure of diginin and diginigenin. J. Chem. Soc. (1962), pp. 3610-3624.
  156. Shoppee, C.W., Lack, Ruth E. Steroids. XVIII. The preparation of some 11-ethynyl steroids. J. Chem. Soc. (1962), pp. 3624-3629.
  157. Shoppee, C.W., Lack, Ruth E., Sternhell, S. Steroids. XIX. The structure of digifolein and digifologenin. J. Chem. Soc. (1963) (June), pp. 3281-3286.
  158. Shoppee, C.W., Bellas, T.E. Steroids and Walden inversion. LII. The bromination of 5a-cholestan-2-one. J. Chem. Soc. (1963) (June), pp. 3366-3371.
  159. Shoppee, C.W., Roy, S.K. I gave II and III. VI. Beckmann rearrangement of some a-hydroxy ketoximes. J. Chem. Soc. (1963), pp. 3774-3777.
  160. Lack, Ruth, Newman, B.C., Shoppee, C.W. The chemical constituents of the leaves of Digitalis lanata. Australian J. Chem. 16 (1963), pp. 896-899.
  161. Mirrington, R.N., Ritchie, E., Shoppee, C.W., Taylor, W.C., Sternhell, S. Constitution of radicicol. Tetrahedron Letters (1964), pp. 365-370.
  162. Shoppee, C.W., Akhtar, M.I., Lack, Ruth E. Steroids. XX. Stereochemistry of homolytic addition of thioacetic acid to olefins of the cholestane series. J. Chem. Soc. (1964), pp. 877-882.
  163. Shoppee, C.W. Chemistry of the Steroids. 2nd ed. (Butterworths: London) 1964, 344 pp.
  164. Shoppee, C.W., Johnson, F.P., Lack, Ruth, Sternhell, S. Long-range spin-spin coupling involving the angular methyl groups in steroids. Tetrahedron Letters (1964), pp. 2319-2322.
  165. Shoppee, C.W., Lack, Ruth E., Newman, B.C. Aza steroids. VII. 3-Aza-A-homopregn-4a-ene and related compounds. J. Chem. Soc. (1964), pp. 3388-3392.
  166. Shoppee, C.W., Akhtar, M.I., Lack, Ruth E. Aza steroids. VIII. 7a-Aza-B-homo-5•-cholestane and 7a-aza-B-homocholest-5-ene. J. Chem. Soc. (1964), pp. 3392-3395.
  167. Shoppee, C.W., Lack, Ruth E. Steroids. XXI. The structure of digacetigenin. J. Chem. Soc. (1964), pp. 3611-3618.
  168. Shoppee, C.W. Digitanol glycosides and aglycons. Symp. Phytochem., Proc. Meeting Univ. Hong Kong (1964), pp. 86-92.
  169. Shoppee, C.W., Havlicek, P.J., Lack, Ruth E. Steroids. XXIII. The polyhalogenation of 5a-cholestan-3-one. J. Chem. Soc. (1964), pp. 4992-4995.
  170. Shoppee, C.W., Lack, Ruth E., McLean, Berwyn. Steroids and Walden inversion. LIII. Substitution reactions of the 3b-acetoxy-, 3a-acetoxy-, 3b-chloro-, and 3a-chloro-5a-cholestan-6a-ols: some further examples of Walden retention. J. Chem. Soc. (1964), pp. 4996-5002.
  171. Shoppee, C.W., Mander, L.N. Azasteroids. IX. Approaches to the partial synthesis of 11-azaprogesterone. J. Chem. Soc. (1965), pp. 1971-1979.
  172. Shoppee, C.W., Johnson, F.P., Lack, Ruth E., Rawson, R. J., Sternhell, S. Steroids. XXIV. The preparation and nuclear magnetic resonance spectra of some 6-substituted 4-methylcholest-4-enes. J. Chem. Soc. (1965), pp. 2476-2482.
  173. Shoppee, C.W., Bellas, T.E., Lack, Ruth E., Sternhell, S. Steroids. XXV. The stereochemistry of ring A and the nuclear magnetic resonance spectra of some steroidal a-halo ketones. J. Chem. Soc. (1965), pp. 2483-2489.
  174. Shoppee, C.W., Holley, T.F., Newsoroff, G.P. Steroids and Walden inversion. LIV. The Grignard oxygenation of epicholesteryl bromide and partial synthesis of 3a-hydroxycholest-6-ene. J. Chem. Soc. (1965), pp. 2349-2354.
  175. Shoppee, C.W., Johnson, F.P., Lack, R.E., Sternhell, S. Line width of N.M.R. signals due to tertiary methyl groups. Chem. Commun. (1965), p. 347.
  176. Shoppee, C.W., Coll, J.C., Hughes, N.W., Lack, R.E. Modification of the 14a-methyl group in lanosterol. Tetrahedron Letters (1965), pp. 3249-3251.
  177. Shoppee, C.W., Bellas, T.E., Lack, Ruth. Steroids and Walden inversion. LV. 2a-and 2b-Chloro-5a-cholestane, and 3a-chloro-5-methyl-5b-cholestane. J. Chem. Soc. (1965), pp. 6450-6458.
  178. Shoppee, C.W., Devine, A.B., Lack, R.E. Steroids and Walden inversion. LVI. The bromination of 5b-cholestan-3-one. J. Chem. Soc. (1965), pp. 6458-6463.
  179. Shoppee, C.W., Lack, R.E., Ram, P. Steroids and Walden inversion. LVIII. Deamination of 3•-and 3a-amino-5a-cholestane. J. Chem. Soc. C (1966), pp. 1018-1023.
  180. Shoppee, C.W., Ram, P., Roy, S.K. Steroids and Walden inversion. LIX. Reactions of some steroid a-hydroxyamines. J. Chem. Soc. C. (1966), pp. 1023-1026.
  181. Mirrington, R.N., Ritchie, E., Shoppee, C.W., Sternhell, S., Taylor, W.C. Some metabolites of Cylindrocarpon radicicola: the structure of radicicola (monorden). Australian J. Chem. 19 (1966), pp. 1265-1284.
  182. Shoppee, Charles W., Hummer, J.K., Lack, Ruth E., Ram, Phulgan, Roy, Sushil Kumar. Steroids and Walden inversion. LVII. Deamination of some allylic amines. Tetrahedron, Suppl. 7 (1966), pp. 315-323.
  183. Shoppee, Charles W., Hughes, N.W., Lack, Ruth E. Synthesis of 3b-hydroxy-4,4-dimethyl-5a-cholest-8-en-11-one from lanosterol. Tetrahedron Lett. (1966), pp. 5235-5237.
  184. Shoppee, Charles W., Hughes, N.W., Lack, Ruth E. Steroids. XXVII. Modification of 14a-methyl group in 4,4,14A-trimethyl steroids. J. Chem. Soc. C. (1966), pp. 2359-2365.
  185. Shoppee, Charles W., Lack, Ruth E., Newman, Barry C. Steroids. XXVIII. Structure of digacetigenin: comparative experiments with ruscogenin and related compounds. J. Chem. Soc. C. (1967) (5), pp. 339-343.
  186. Shoppee, Charles W., Johnson, Frank Patrick, Lack, Ruth E., Shannon, James S., Sternhell, Sever. Line widths of nuclear magnetic resonance signals of tertiary methyl groups. Tetrahedron, Suppl. 8 (Part II) (1966), pp. 421-442.
  187. Shoppee, Charles W., Lack, Ruth E., Sharma, S.C., Smith, Lorraine R. Steroids and Walden inversion. LX. Some reactions of the epimeric 5a-cholestan-1-ols and the solvolysis of their toluene-p-sulfonates. J. Chem. Soc. C. (1967), pp. 1155-1159.
  188. Shoppee, Charles W., Hughes, N.W., Lack, Ruth E., Newman, Barry C. The structure of digacetigenin. Tetrahedron Lett. (1967), pp. 3171-3174.
  189. Shoppee, Charles W., Sharma, S.C. Steroids and Walden inversion. LXI. Chlorination of 5a-cholestan-2-one. J. Chem. Soc. C. (1967), pp. 2385-2391.
  190. Shoppee, Charles W., Sharma, S.C. Steroids and Walden inversion. LXII. Chlorination of 5a-cholestan-1-one. J. Chem. Soc. C. (1968), pp. 245-249.
  191. Shoppee, Charles W., Hughes, N.W., Lack Ruth E. Steroids. XXIX. Structure of digacetigenin. J. Chem. Soc. C. (1968), pp. 786-793.
  192. Shoppee, Charles W., Newman, Barry C. Steroids. XXX. Properties of the cholest-5-ene-3b,7x-diols and their esters. J. Chem. Soc. C. (1968), pp. 981-983.
  193. Shoppee, C.W., Coll, J.C., Lack, Ruth E. Steroids. XXXI. Attempted modification of the 14a-methyl group in 4,4,14a-trimethyl steroids. J. Chem. Soc. C. (1968), pp. 1581-1585.
  194. Shoppee, C.W., Lack, R.E., Sharma, S.C. Steroids and Walden inversion. LXIII. Substitution reactions of 5a-cholestan-4-ols: a further example of Walden retention. J. Chem. Soc. C. (1968), pp. 2083-2086.
  195. Shoppee, C.W., Feher, J. G., Hall, R.M., Lack, R.E., Tarasoff, L., Jr. Steroids and Walden inversion. LXIV. A reinvestigation of the deamination of 2a,4a, and 7b-amino-5a-cholestane. J. Chem. Soc. C. (1968), pp. 2211-2215.
  196. Shoppee, C.W., Hughes, N.W., Lack, Ruth E. The structure of digacetigenin. Tetrahedron Lett. (1968), pp. 3897-3899.
  197. Shoppee, Charles W., Culshaw, Christina, Lack, Ruth E. Steroids and Walden inversion. LXV. Comparative experiments on the deamination of cis-and trans-4-tert-butylcyclohexylamine. J. Chem. Soc. C. (1969), pp. 506-508.
  198. Shoppee, Charles W., Lack, Ruth E. Intramolecular electrocyclic reactions. I. Structure of 'bromohydroxphorone': 3-bromo-5-hydroxy-4,4,5,5-tetramethylcyclopent-2-enone. J. Chem. Soc. C. (1969), pp. 1346-1349.
  199. Shoppee, Charles W., Coll, J.C. Steroids. XXXII. Epoxidation of 3b-acetoxy-5a-lanosta-7,9(11)-diene. J. Chem. Soc. C. (1969), pp. 2157-2158.
  200. Shoppee, Charles W., Newman, Barry C. Steroids and Walden inversion. LXVI. 5b,14a-Androst-15-en-17-one. J. Chem. Soc. C. (1969), pp. 2767-2770.
  201. Shoppee, Charles W., Bellas, T.E., Coll, J.C., Lack, Ruth E. Steroids. XXXIII. Attempted preparation of 19-nor-5a-cholestanes via 2b-hydroxy-5a-cholestan-19-oic acid. J. Chem. Soc. C. (1969), pp. 2734-2738.
  202. Shoppee, Charles W., Hughes, N.W., Newman, Barry C. Steroids. XXXIV. 17b-Hydroxy-5b,14a,17a-pregnan-20-one and related compounds. J. Chem. Soc. C. (1970), pp. 558-560.
  203. Shoppee, Charles W., Coll, J.C. Steroids and Walden inversion. LXVIII. Reexamination of the substitution reactions of the 5a-cholestan-3-ols. J. Chem. Soc. C. (1970), pp. 1124-1125.
  204. Shoppee, Charles W., Hughes, N.W., Lack, Ruth E., Pinhey, J.T. Steroids. XXXV. Removal of the 4-methyl groups in 4,4,14•-trimethylsteroids: conversion of lanosterol into 14a-methylcholest-4-en-3-one. J. Chem. Soc. C. (1970), pp. 1443-1447.
  205. Shoppee, Charles W., Coll, J.C. Steroids and Walden inversion. LXVII. Substitution reactions of the 19-nor-5a-cholestan-2-ols. J. Chem. Soc. C. (1970), pp. 1121-1123.
  206. Shoppee, Charles W., Killick, R.W. Steroids. XXXVI. Some 13,17-secoandrostanes. J. Chem. Soc. C. (1970), pp. 1513-1514.
  207. Shoppee, Charles W., Coll, J.C., Lack, Ruth E. Steroids. XXXV. Preparation of the epimeric 2-hydroxy-19-nor-5a-cholestanes. J. Chem. Soc. C. (1970), pp. 1893-1900.
  208. Shoppee, Charles W., Coll, J.C., Lack, Ruth E. Mass spectra of some C-19 modified 5a-cholestane derivatives. Org. Mass Spectrom. 4 (Suppl.) (1970), pp. 373-382.
  209. Shoppee, C.W., Hughes, N.W., Sternhell, S. Octamethyl 2,2,4,4-tetracarboxy-1,3-cyclobutanedimalonate. J. Chem. Soc. C. (1971), pp. 3679-3681.
  210. Shoppee, C.W., Hughes, N.W. Structures of 1,5-hexadiene-1,1,3,3,4,4,6,6-octacarboxylic esters. J. Chem. Soc. C. (1971), pp. 3673-3679.
  211. Shoppee, C.W., Cooke, B.J.A. Intramolecular electrocyclic reactions. II. Reactions of 1,5-diphenyl-1,4-pentadien-3-one. J. Chem. Soc., Perkin Trans. 1 (1972), pp. 2271-2276.
  212. Shoppee, C.W., Stevenson, D. 2,2,6,6-Tetramethyl-3,4,5-heptanetrione. J. Chem. Soc., Perkin Trans. 1 (1972), pp. 3015-3020.
  213. Shoppee, Charles W. Christopher Kelk Ingold, 1893-1970. Biogr. Mem. Fellows Roy. Soc. 18 (1972), pp. 349-411.
  214. Shoppee, C.W., Nemorin, J. Steroids and Walden inversion. LXIX. Substitution reactions of the 5a-androstan-11-ols. J. Chem. Soc., Perkin Trans. 1 (1973), pp. 542-545.
  215. Shoppee, Charles W., Cooke, Burgess J.A. Electrocyclic reactions. III. Reactions of 2,4-dimethyl-1,5-diphenyl-1,4-pentadien-3-one (a,a'-dimethyldibenzylideneacetone). J. Chem. Soc., Perkin Trans. 1 (1973), pp. 1026-1030.
  216. Shoppee, Charles W., Cooke, Burgess J.A. Electrocyclic reactions. IV. Reactions of 2,4-dibromo-1,5-diphenylpenta-1,4-diene-3-one(a,a' dibromodibenzylideneacetone). J. Chem. Soc., Perkin Trans. 1 (1973), pp. 2197-2202.
  217. Shoppee, Charles W., Cooke, Burgess J.A. Electrocyclic reactions. V. Structure of the product from trans, trans-dibenzylideneacetone and sulfuric acid-acetic anhydride. J. Chem. Soc., Perkin Trans. 1 (1974), pp. 189-190.
  218. Shoppee, Charles W., Henderson, George N. Electrocyclization of the 1,5-diphenylpenta-1,4-dienyl anion. J. Chem. Soc., Chem. Commun. (1974), pp. 561-562.
  219. Shoppee, Charles W., Henderson, George N. Electrocyclic reactions. VI. Thermal reactions of 1,5-diphenylpentadienide ion and the anions derived from cis-and trans-3,4-diphenylcyclopentene. J. Chem. Soc., Perkin Trans. 1 (1975), pp. 765-772.
  220. Shoppee, Charles W., Wang, Yueh-Sha. Electrocyclic reactions. VII. Irradiation of 3,5-dibromo-2,6-dimethylhepta-2,5-dien-4-one (a,a'-dibromophorone). J. Chem. Soc., Perkin Trans. 1 (1975), pp. 1595-1600.
  221. Alcock, Nathaniel W., Herron, Norman, Kemp, Terence J., Shoppee, Charles W. Orientation of photodimerization by metal ions. Crystal structure of bis(dibenzylideneacetone)uranyl dichloride. J. Chem. Soc., Chem. Commun. (1975), pp. 785-786.
  222. Shoppee, Charles W., Cooke, Burgess J.A. Electrocyclic reactions. VIII. Reactions of trans, trans-and cis, trans-2-bromo-1,5-diphenylpenta-1,4-dien-3-one (a-bromodibenzylideneacetone). J. Chem. Soc., Perkin Trans. 1 (1975), pp. 2210-2215.
  223. Shoppee, Charles W., Lundberg, Robert D. Steroids and Walden inversion. LXX. Re-examination of the substitution reactions of 5a-cholestan-6a-ol. J. Chem. Soc., Perkin Trans. 1 (1975), pp. 2205-2208.
  224. Shoppee, Charles W., Lundberg, Robert D. Steroids. XXXVIII. 5-Chloro-5a-cholestane. J. Chem. Soc., Perkin Trans. 1 (1975), pp. 2208-2210.
  225. Shoppee, Charles W., Lundberg, Robert D. Reaction of 5a-cholestan-6a-ol with phosphorus pentachloride and with thionyl chloride. Steroids, 26 (1975), pp. 470-476.
  226. Shoppee, Charles W., Wang, Yueh-Sha. Electrocyclic reactions. Part IX. Photolysis of trans, trans-2,4-dibromo-1,5-diphenylpenta-1,4-dien-3-one (a,a'-dibromodibenzylideneacetone). J. Chem. Soc., Perkin Trans. 1 (1976), pp. 695-704.
  227. Shoppee, Charles W., Wang, Yueh-Sha, Sternhell, Sever, Brophy, Graham C. Electrocyclic reactions. Part X. Photochemical cyclization of trans, trans-dibenzylideneacetone. J. Chem. Soc., Perkin Trans. 1 (1976), pp. 1880-1886.
  228. Shoppee, Charles W. Electrocyclic reactions of some penta-1,4-diene systems. Heterocycles, 5 (1976), pp. 605-630.
  229. Shoppee, Charles W., Henderson, George N. Electrocyclic reactions. Part 11. 1,5-Diphenylpentadienide. J. Chem. Soc., Perkin Trans. 1 (1977), pp. 1028-1030.
  230. Shoppee, Charles W., Hart, Reinhold J., Howden, Merlin E.H. Steroids. Part 39. 5-Chloro-5b-cholestane. J. Chem. Soc., Perkin Trans. 1 (1980), pp. 1904-1908.
  231. Shoppee, Charles W. 5-Chloro-5b-cholestane, the first simple 5b-chloro steroid. J. Steroid Biochem. 19 (1983), pp. 777-7781.
  232. Shoppee, Charles W., Hart, Reinhold J. Electrocyclic reactions. Part 12. 1,5-Diphenylpentadienide-2,3,4-2H3 anion in the Caglioti reaction. J. Chem. Soc., Perkin Trans. 1 (1983), pp. 2369-2373.
  233. Shoppee, Charles W. Photochemical transformation of tetrabromofuran by oxygen into 2,3,4,4-tetrabromo-2-buten-4-olide in the solid state. J. Chem. Soc., Perkin Trans. 1 (1985), pp. 45-52.
  234. Shoppee, Charles W., Brownlee, Robert T.C. NMR spectra of the b-methylcinnamic acids and their methyl esters. Australian J. Chem., 38 (1985), pp. 1557-1559.
  235. Shoppee, Charles W., Wu, Wen Yang. Photooxidation of tetrabromofuran in benzene. Australian J. Chem., 40 (1987), pp. 1137-1144.

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