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Biographical :7Vfemoirs VOLUME 53

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- c . - D o U' C) o PA 5- o ~0

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ROGER ADAMS January 2, 1889-July 6, 1971 BY D. STANLEY TARBELL AND ANN TRACY TARBELL ROGER ADAMS was for a generation the leacling organic chemist in the United States. In addition to publishing outstanding research in structural chemistry anti stereo- chemistry and to training about 250 Ph.D.'s and postdoc- torates at Illinois, he player! a key role in the development of graduate education in science. His influence on the growth of industrial chemical research was great, both personally and through the students he trained. His services to the country in two world wars and to the scientific community brought him the role of scientific statesman on the world scene. He combined personal qualities of charm, strength, high intelli- gence, and extraordinary capacity for hard work. Roger Adams was a direct descendant of the uncle of President John Adams; his ancestors had moved to south- eastern New Hampshire, where Roger's father, Austin W. Adams (1845-1916), was born. Austin taught in a country school, then movect to Boston in IS72, where he was asso- ciated with the Old Colony and New Haven Railroads for the rest of his life. In 1880 he married Lydia Curtis from Jamaica Plain, likewise a school teacher, who was related to numerous business and literary figures in Boston and was clescencled from early colonial settlers. The Adamses lived for twenty years on Worcester Street 3

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4 BIOGRAPHICAL MEMOIRS in the then attractive residential section of South Boston. Austin Adams, a kink! father and a man with scholarly avoca- tions, supported his family on a comfortable but not lux- urious scale. Roger was the last child in a family with three daughters, and he apparently had a happy boyhood. Two of Roger's sisterstall, athletic, and gifted graduated from Racicliffe and the third from Smith. The family moved to Cambridge in 1900, probably to be nearer the colleges. After preparation at Boston Latin anct Cambridge Latin, Roger entered Harvard in 1905. His first years were un- distinguished acaclemically, but he completed the require- ments for his A.B. in chemistry in three years, earning high grades in his major courses in chemistry and in his minor of mining. His interest in chemistry may have been aroused by C. L. ~ackson's course on "the chemistry of common life," which he took in his first year. He worked very hard at a series of demancling courses and had the satisfaction of re- ceiving a John Harvard honorary scholarship for making four A's. In his last unclergracluate year he took advanced courses anti started research in organic chemistry with H. A. Torrey. After graduation in 1909, he worked for his Ph.D., aided by a teaching assistantship at Radcliffe. Torrey cliecl prematurely in 1910, anct Adams completed his thesis with the help of Jackson, Latham Clarke, ant! G. S. Forbes. Among his fellow graduate students in 1911 ant! 1912 were E. K. Bolton ("Keis," a close friend), Farrington Daniels, Frank C. Whitmore, and James B. Sumner. James B. Conant was then an unclergraduate. As an outstanding Ph.D. of 1912, Aciams was awarded a Parker Traveling Fellowship for 1912 and 1913, which he spent partly in the laboratory of Emil Fischer with Otto Diels at Berlin and partly with the brilliant Richard WilIstatter in the latter's new laboratory in DahIem, near Berlin. A ticket stub among Adams' papers shows that he took a Zeppelin

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ROGER ADAMS flight from Potsdam to Berlin; he also traveled in Finland, Russia, ant! Sweden. Although it resulted! in no scientific papers, Adams' Euro- pean year was the beginning of his lifelong interest in 5 , , ~ At_ European science and scientists. He clearly found the Euro- pean university system clistasteful; one professor in each department or institute controlled absolutely the activities of all research students and junior staff members. This attitude is reflected in Adams' leadership of the Illinois department along more democratic lines, which provided a mode] for other graduate science departments in American universi- ties. Adams' policy of helping his junior colleagues develop inclepenclent research careers was emphasized further in 1954, when he clesigne`1 the program for the Sloan Founcla- tion that gave unrestricted grants to promising younger workers. As a result of his foresight, generations of young American scientists are in his debt. Adams returned to Harvard in 1913 as research assistant to C. L. Jackson at $800 a year and shortly undertook the duties of instructor in chemistry. Along with other courses he taught elementary organic chemistry and initiated the first elementary laboratory in that subject at Harvard. He was a very successful teacher, so much so that James B. Conant, who succeeded him, die! so with some trepidation about his own ability to interest an elementary class in organic chem- istry. During his three years on the Harvard faculty, Adams not only carried a very heavy formal teaching load at Har- varcl and Radcliffe, but made a strong start on his own re- search program. In 1916 Adams accepted an offer from William A. Noyes, head of the Illinois Chemistry Department, to become assis- tant professor at a salary of $2,\800 per year. He was ambi- tious to accomplish something notable in science; he un- doubtedly saw that the Illinois department, aIreacly well

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6 BIOGRAPHICAL MEMOIRS known for its research and teaching under Noyes' leadership, offered greater opportunities than Harvard, as well as better laboratory facilities and the challenge of a position outside New England. He took the position at Illinois with no reser- vations and with the determination to develop his own research program and that of the department. Urbana re- mained his home for the rest of his life, in spite of many attractive offers to move to industry or university positions, including MIT and Harvard. It is indicative of his personal dedication to Illinois as his residence that he later joined the Rotary Club and served as its president in 1932. At TIlinois Adams took charge of the important "prep labs" started by his predecessor, C. G. Derick, for the syn- thesis of essential organic chemicals cut off by the blockade of Germany. This was expanded and, with the help of graduate students, particularly E. H. Volwiler and C. S. (Speed) Mar- vel, over 100 key compounds were made available for sale and for use in Illinois. Adams reorganized the operation, introduced strict cost accounting procedures, and made it a financial as well as scientific success. The tested procedures developed in "preps" (officially called Organic Chemical Manufactures) led to the indispensable annual publication, Organic Syntheses, of which fifty annual volumes were pub- lished under Adams' watchful eye. Conant later said that the publication should have been named "Adams Annual," . . . because he was the moving spirit. At Urbana Adams pursued research vigorously on the preparation of local anaesthetics with Oliver Kamm of the Illinois faculty and became a consultant to Abbott in 1917, a relationship that lasted on a formal basis until the 1960's. E. H. Volwiler, his first Ph.D., joined Abbott as a research chemist in 1918. Adams was drawn into research for the army in 1917 and, with other chemists, worked on problems connected with war

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ROGER ADAMS 7 gases at American University in Washington, D.C. Adams and Conant headed research groups, and E. P. KohIer, Adams' old faculty friend from Harvarcl, was in charge of the Offense Section. Adams spent the last few months of 1918 in uniform as a major. He was recognized by Conant as the leading figure in the group. Adams was married to Lucile Wheeler on August 29, 1918 at White River {unction, Vermont. Mrs. Adams came from a well-known Vermont family; she was a Mount Holy- oke graduate, had studiecI dietetics at Columbia, and tract taught home economics at TIlinois. They tract one child, Lu- cile, and there are four grandchildren, in whom Aciams clelighted, particularly in his retirement years. The Adamses soon moved to a large house at 603 West Michigan, Urbana, where many guests, students and ctistinguished visitors alike, were graciously entertained by Mrs. Aciams. This house was Adams' headquarters for the rest of his life. He wrote fre- quently to Mrs. Adams when he was away; he had a gift for light verse and sent a rhymed valentine to her and their daughter each year. Adams' return to Urbana was followed by intensive re- search with a large number of Ph.D. students ancI by many outstanding scientific publications. From 1918 through 1926 he publishect seventy-three scientific papers and trained forty-five Ph.D.'s, including E. H. Volwiler, I. R. Johnson, A. W. Ingersoll, S. M. McEIvain, W. H. Carothers, W. R. Brode, C. R. Noller, R. L. Shriner, C. F. Rassweiler, and many others who became well known in academic or industrial chemistry. This was in spite of a very serious illness in 1924, recovery from which required nearly a year. During this time he took up stamp collecting, a hobby he pursued for many years with characteristic thoroughness ancl enthusiasm. The important problems he worked on during his re- search career included the development of platinum oxide

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8 BIOGRAPHICAL MEMOIRS for catalytic hydrogenation (Adams catalystdiscovered by an excellent example of serendipity), local anaesthetics, syn- thesis of naturally occurring anthraquinones, structure and synthesis of chaulmoogric acid (used at that time in treating leprosy), stereochemistry of compounds with restricted rota- tion and of deuterium compounds, the structure of gossypo} (the yellow material in cottonseed meal), compounds isolated from marihuana, and the structure of the Crotalaria and Senecio alkaloids and quinoneimines. The gossypo] structure was perhaps the most difficult, but the voluminous cor- respondence related to his work on marihuana illustrates well the administrative and scientific ability and the bound- less energy and enthusiasm with which he pursued his researches. As a body, Adams' research represents the high point of structural organic chemistry, particularly on natural prod- ucts, before the Instrumental Revolution and before the emergence of physical organic chemistry as a major field. He was elected to the National Academy of Sciences in 1929. In 1926 Adams was chosen unanimously to succeed! W. A. Noyes as head of the Chemistry Department at Illinois. By this date the department was recognized as one of the leaders in organic chemistry, and the characteristic features of Adams' conception of a graduate department were clear. The faculty should be of outstanding ability: Adams, Marvel, R. L. Shriner, R. C. Fuson, and, in the 1930's and later, H. R. Snyder, C. C. Price, N. J. Leonard, and their junior col- leagues formed the organic group, with few changes. Equip- ment and facilities were to be kept up to date; graduate students and undergraduates were carefully selected ancT were caught up in the infectious enthusiasm and hard work of the faculty so that they, too, worked long hours. Research was carefully done? carefully and promptly prepared for publication, and great attention was paid to placing graduates

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ROGER ADAMS 9 in suitable positions. Adams was actively interested in the progress of all Illinois graduates in chemistry after they left Urbana and recommended them for new positions as the occasion arose; his remarkable memory enabled him to call most of them by name, whoever had directed their research. Adams developed a highly successful scheme for direct- ing graduate student research. By starting a student on a problem that promised reasonable success and by publishing the work promptly, he built up the stuclent's confidence to undertake more difficult experiments. Such problems as hin- dered rotation in biphenyIs offered indispensable and excel- lent training in synthesis and physical measurements, and clifficult investigations in natural products were usually given to experienced graduate students or to postdoctorates. Adams' personal magnetism macle interesting even the drudgery encountered in research projects, and macle good results exciting. His buoyant and forward-Iooking nature, his outgoing personality, his interest in people as individuals, and his breadth of knowledge and experience made conver- sation with him amusing and delightful, broadly eclucational in the best sense. Aclams' work on Organic Syntheses, his circulation of bound volumes of reprints to leacling universities here and abroad, and his active participation in scientific societies increased the reputation of his department. What he had really accom- plished by 1930 was the development of a graduate clepart- ment of national stature that had strength in all significant fields of chemistry; it represented a novel addition to that characteristic American educational institution, the land- grant college. Although A. A. Noyes at MIT (later at Caltech) and G. N. Lewis at Berkeley hac! built up departments of physical chemistry with several outstanding colleagues, the Illinois department was larger and offered a broader range of research opportunities to students.

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10 BIOGRAPHICAL MEMOIRS The growth and research output of the Illinois depart- ment are shown by a survey of papers in organic chemistry in the Journal of the American Chemical Society. In the twenty-five years from 1914 through 1939, Illinois was surpassed only four times in number of publications of organic research, advancing from four papers in 1914 to sixty-six papers in 1939, Il percent of all organic papers published in this journal from all the nation's laboratories in ~ 939. The Illinois papers were scientifically of high quality. Although figures available do not give cloctorates for organic chemistry as such, cluring the years 1920 through 1939 Illinois producer! 346 Ph.D.'s in chemistry, 6 percent of all American Ph.D.'s in this field. Adams clirected almost one-third of the TIlinois total ant! accounted for about 2 percent of those in the whole country for the years 1920 through 1939, as shown in the following table; during the li920's Adams trained 3 percent of the American Ph.D.'s in all fields of chemistry. Doctorates Granted in All Fields of Chemistry, 1920-1939 Years Illinorsa Total US 192~1924 64 (30) 746 1925-1929 73 (26) 1,178 193~1934 103 (25) 1,751 1935-1939 106 (22) 2,212 a Figures in parentheses represent Adams' own Ph.D.'s for these periods. Of the 105 Ph.D.'s trained by Adams during the years 191~ through 1939 inclusive, seven were women; of the total, fifty-nine spent most or all of their careers in inclustrial re- search, twenty-six were in teaching, and nine worked in gov- ernment laboratories. The remainder included a number of overseas students. Where did all of these chemists find jobs? Consideration of this question leads to Roger Adams' interaction with the

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ROGER ADAMS 11 industrial chemical research community, which grew strik- ingly between the two florid wars. It is estimates! that in ~ 920 there were 300 industrial research laboratories in the United States, and that in 1940 the number had grown to 2,200. In 1927 the chemical industry is believed to have hac! 3,300 research people, and in 193S, in spite of the depression, the number had increased to 9,542. Adams had a natural inclination toward the business worm; although he always regarded] himself as a member of the academic profession, he understood finance and business and was liked and trustee! by businessmen. He served as consultant for A. E. Staley Co., M. W. Kellogg Co., and Coca-Cola, as well as Abbott, and he and Marvel became consultants for DuPont in 1928. Industrial research was given a large boost by the spectacular success of Adams' bril- liant student, Wallace H. Carothers, whose funciamental re- search on polymers at DuPont from 1928 to 1937 resulted in the discovery of nylon and neoprene rubber. Adams, always close to him, was deeply affected by his death in 1937. Adams frequently wrote and spoke about what industry was entitled to expect from its research chemists, and the majority of Illinois Ph.D.'s who clid go into industrial research were well informed as graduate students in this regard. Con- versely, he was able to make clear to research management in industry how research chemists should be treated to maintain good morale and productivity. As the number of Illinois Ph.D.'s grew, it was a small educational or industrial labora- tory that did not have one or more. Hence, the influence of the Illinois department and its graduates became very great, particularly when many of these graduates reached respon- sible administrative positions in research and teaching. Adams was constantly being asked for advice about academic and industrial positions everywhere, and he spent much ef- fort in fancying suitable positions for his students. In 1954 he

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ROGER ADAMS 37 With Z. W. Wicks. 2,3,5,8-Tetramethoxy-6,7-dimethyl- 1-naph- thaldehyde. I. Am. Chem. Soc., 66: 1315-16. 1945 With S. I. Cristol, A. W. Anderson, and A. A. Albert. The structure of leucenol. I. }. Am. Chem. Soc., 67:89-92. With R. S. Ludington. Restricted rotation in aryl olefins. IX. Effect of various substituents on the olefin grouping. I Am. Chem. Soc., 67:794-97. With i. W. Mecorney. Restricted rotation in aryl olefins. X. ,8-methyl-,3-arylacrylic acids. l. Am. Chem. Soc., 67:798-802. With K. H. Chen and S. Loewe. Tetrahydrocannabinol homologs with a s-alkyl group in the 3-position. XVI. I. Am. Chem. Soc., 67: 1534-37. 1947 With V. V. Jones. The structure of leucenol. II. l. Am. Chem. Soc., 69: 1803-5. With T. R. Govindachari. The structure of leucenol. III. Synthesis of 2,5-dihydroxypyridine (5-hydroxy-2-pyridone). }. Am. Chem. Soc., 69:1806-8. With V. V. Jones and }. L. Johnson. The structure of leucenol. IV. J Am. Chem. Soc., 69:1810-12. 1948 With B. F. Aycock, Jr. and S. Loewe. Tetrahydrocannabinol homo- logs. XVII. I. Am. Chem. Soc., 70:662-64. With S. MacKenzie, Jr. and S. Loewe. Tetrahydrocannabinol homologs with doubly branched alkyl groups in the 3-position. XVIII. }. Am. Chem. Soc., 70:664-68. With Jean Mathieu. A new synthesis of atranol (2,6-dihydroxy-4- methylbenzaldehyde) and the corresponding cinnamic acid. }. Am. Chem. Soc., 70:2120-22. With N. K. Sundholm. Restricted rotation in aryl amines. IV. Prep- aration and resolution of N-succinyl- 1-methylamino-2,4-di- methyl-6-substituted benzenes. }. Am. Chem. Soc., 70:2667-73. With R. G. Chase. Restricted rotation in substituted aromatic amines. V. Derivatives of N,N'-dimethyldiaminomesitylene. I. Am. Chem. Soc., 70:4202-4.

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38 BIOGRAPHICAL MEMOIRS With l. I. Tjepkema. Restricted rotation in substituted aromatic amines. VI. Stereoisomers of N,N'-dialkyl-N,N'-dibenzenesul- fonyl-diaminomesitylene. l. Am. Chem. Soc., 70:420~13. 1949 Restricted rotation. Rec. Chem. Frog., 10:91-99. With }. Hine and }. Campbell. Triarylpyridylmethanes. I. Am. Chem. Soc., 71:387-90. With R. D. Lipscomb. Amine bisulfite addition products of alde- hydes and ketones. I. I. Am. Chem. Soc., 71:519-22. With I. D. Garber. Amine bisulfites. II. Their use as resolving agents for aldehydes and ketones. }. Am. Chem. Soc., 71:522-26. With l. L. Johnson. Leucenol. VI. A total synthesis. I. Am. Chem. Soc., 71: 705-8. With T. R. Govindachari. Senecio alkaloids: cat- and ,l3-longilobine from Senecio longilobus. J. Am. Chem. Soc., 71: 118~86. With A. W. Schrecker. Condensation reactions of N-substituted pyridones. J. Am. Chem. Soc., 71:118~95. With M. Rothstein. Restricted rotation in substituted aromatic amines. VII. Stereoisomers of N,N'-dimethyl-N,N'-diarylsul- fonyldiamino mesitylenes. I. Am. Chem. Soc., 71:162() 23. With M. Harfenist and S. Loewe. New analogs of tetrahydrocanna- binol. XIX. I. Am. Chem. Soc., 71:1624-28. With T. R. Govindachari. Senecio alkaloids: the isolation of senecio- nine from Senecio cineraria and some observations on the struc- ture of senecionine. I. Am. Chem. Soc., 71: 1953-56. With T. R. Govindachari. Senecio alkaloids: the alkaloids of Senecio douglasii, carthamoides, eremophilus, ampullaceus and parksii. ]. Am. Chem. Soc., 71: 195~60. With W. Herz. Helenalin. I. Isolation and properties. J. Am. Chem. Soc., 71:254~51. With W. Herz. Helenalin. II. Helenalin oxide. I. Am. Chem. Soc., 71:2551-54. With W. Herz. Helenalin. III. Reduction and dehydrogenation. J. Am. Chem. Soc., 71:2554-59. With I. B. Campbell. 2-Triphenylmethylaminopyridine. J. Am. Chem. Soc., 71:3539-42. With V. V. Jones. Addition and condensation reactions of 2-py- ridone. l. Am. Chem. Soc., 71:382~33.

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ROGER ADAMS 1950 39 With }. B. Campbell. Restricted rotation in aryl amines. VIII. Ring nitrogen derivatives of diaminomesitylene. }. Am. Chem. Soc., 72: 128-32. With N. K. Nelson. Restricted rotation in aryl amines. IX. Diamino- durene derivatives. I. Am. Chem. Soc., 72:132-35. With B. Englund. Restricted rotation in aryl amines. X. Stereoi- somers of N,N',N "-trialkyl-N,N',N "-tribenzenesulfonyltri- amino-mesitylenes. l. Am. Chem. Soc., 72: 13~38. With l. Campbell. Hindered tetraarylmethanes. I. Am. Chem. Soc., 72: 15~55. With W. Herz. Synthesis of viridifloric acid. l. Am. Chem. Soc., 72: 15~57. With T. R. Govindachari. Structure of monocrotaline. XII. Mono- crotalic acid. I. Am. Chem. Soc., 72: 158-63. With W. M. Whaley. The amaroids of quassia. I. Quassin, isoquas- sin and neoquassin. I. Am. Chem. Soc., 72:375-79. With }. Campbell. 2,4,5- and 2,4,7-trimethylquinolines. }. Am. Chem. Soc., 72:1021-22. With F. L. Warren, M. Kropman, T. R. Govindachari, and I. H. Looker. The identity of,l3-longilobine with retrorsine. }. Am. Chem. Soc., 72: 1421-22. With A. S. Nagarkatti.2,4- and 4,6-dinitro- and diamino~n-xylenes. I Am. Chem. Soc., 72:1831-32. With I. R. Gordon. Restricted rotation in aryl amines. XI. Influence of groups decreasing the basicity of the nitrogen atom. J. Am. Chem. Soc., 72:245~57. With I. R. Gordon. Restricted rotation in aryl amines. XII. Resolu- tion of certain N-benzenesulfonyl-N-carboxymethyl derivatives. }. Am. Chem. Soc., 72:2458-60. With A. S. Nagarkatti. Quinone imides. I. p-Quinone disulfoni- mides. J. Am. Chem. Soc., 72:4601-6. With A. S. Nagarkatti. Restricted rotation in aromatic amines. XIII. The effect of monosubstitution in the ortho position. J. Am. Chem. Soc., 72:460~8. With N. K. Nelson. Restricted rotation in aryl amines. XIV. Iso- propyl derivatives of dibenzenesulfonamidomesitylene. I Am. Chem. Soc., 72:5077-79. With J. L. Johnson and B. Englund. Polymers of c~-acetamidoacrylic acid and its methyl ester. l. Am. Chem. Soc., 72:508(~82.

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40 BIOGRAPHICAL MEMOIRS With T L. Anderson. Quinone imides. II. p-Quinone diacyl and diaroylimides. I. Am. Chem. Soc., 72:515~57. 1951 With R. A. Wankel. Quinone imides. III. 1,4-Naphthoquinone di- sulfonimides. I. Am. Chem. Soc., 73:131-34. With I. H. Looker. The identity of a-longilobine and seneciphyl- line. }. Am. Chem. Soc., 73: 13~36. With I. L. Anderson. The effect of c-methyl substituents on the anhydridization of aliphatic dibasic acids. I. Am. Chem. Soc., 73: 13~41. With i. H. Looker. Quinone imides. IV. p-Quinone monosulfoni- mides. l. Am. Chem. Soc., 73: 114~49. With K. R. Eilar. Quinone imides. V. Aluminum chloride-catalyzed arylations of p-quinone dibenzenesulfonimides. }. Am. Chem. Soc., 73:114~52. With C. R. Walter, {r. Quinone imides. VI. Addition of dienes to p-quinone sulfonimides. i. Am. Chem. Soc., 73:1152-55. With R. A. Wankel. Quinone imides. VII. 1,2- and 2,6-naphtho- quinone disulfonimides. I. Am. Chem. Soc., 73:221~20. With C. N. Winnick. Quinone imides. VIII. Synthesis and reactions of o-quinone diimides. }. Am. Chem. Soc., 73:5687-91. 1952 With F. B. Hauserman. The total structure of monocrotaline. XIII. Synthesis of dihydroanhydromonocrotalic acid. I. Am. Chem. Soc., 74:694-99. With T. R. Govindachari, I. H. Looker, and I. D. Edwards, Jr. Senecio alkaloids: c~-longilobine; structure of c'-longinecic acid. }. Am. Chem. Soc., 74:700-703. With W. Moje. Quinone imides. IX. Addition of dienes to 1,4- naphthoquinonedibenzenesulfonimide. J. Am. Chem. Soc., 74:2593-96. With K. A. Schowalter. Quinone imides. X. Addition of amines to p-quinonedibenzenesulfonimide. J. Am. Chem. Soc., 74: 2597-602. With I. D. Edwards, Jr. Quinone imides. XI. Addition of dienes to p-quinonedibenzenesulfonimide. J. Am. Chem. Soc., 74: 2603-4.

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ROGER ADAMS 41 With }. D. Edwards, Jr. Quinone imides. XII. Addition of dienes to p-quinonemonobenzenesulfonimide. I. Am. Chem. Soc., 74: 2605-7. With E. F. Elslager and K. F. Heumann. Quinone imides. XIII. Orientation of groups in adducts of hydrogen chloride with quinone diimides. I. Am. Chem. Soc., 74:2608-12. With D. S. Acker. Quinone imides. XIV. Addition of hydrogen chloride to p-quinonedibenzimides and related compounds. I. Am. Chem. Soc., 74:3029-32. With R. R. Holmes. Quinone diimides. XV. Diphenoquinonedi- imides. l. Am. Chem. Soc., 74:3033-37. With R. R. Holmes. Quinone diimides. XVI. Diphenoquinonedi- imides. }. Am. Chem. Soc., 74:3038-41. With B. H. Braun. Chlorination of benzenesulfonyl derivatives of aromatic amines. I. Am. Chem. Soc., 74:3171-73. With D. S. Acker. Quinone imides. XVII. Addition of organic acids top-quinonedibenzimide and related compounds. I. Am. Chem. Soc., 74:3657-59. With I M. Stewart. Quinone imides. XVIII. p-Quinonedipival- imides and their reactions. l. Am. Chem. Soc., 74:3660-64. With Irwin }. Pachter. Structure of the 2-pyridone and a-bromoacrylic acid adduct and its derivatives. I. Am. Chem. Soc., 74:4906-9. With B. L. Van Duuren. Trachelanthic and viridifloric acids. I. Am. Chem. Soc., 74:5349-51. With T. E. Bockstahler. Preparation and reactions of o- hydroxycinnamic acids and esters. }. Am. Chem. Soc., 74: 5346-48. With I. I. Pachter. Ultraviolet spectra and structures of the pyridoll,2-a]-pyrimidones. I. Am. Chem. Soc., 74:5491-97. With W. Moje. Quinone imides. XIX. Addition of active methylene compounds to 1,4-naphthoquinonedibenzenesulfonimide. I. Am. Chem. Soc., 74:5557-60. With W. Moje. Quinone imides. XX. Additions to 1,4-naphtho- quinonedibenzenesulfonimide. J. Am. Chem. Soc., 74:5560-62. With W. Moje. Quinone imides. XXI. Addition of hydrogen cya- nide to 1,4-naphthoquinonedibenzenesulfonamide. J. Am. Chem. Soc., 74:5562-63. With R. S. Voris and L. N. Whitehill. Restricted rotation about the aliphatic carbon-carbon bond. }. Am. Chem. Soc., 74:5588-92.

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42 BIOGRAPHICAL MEMOIRS With B. L. Van Duuren and B. H. Braun. The structure of mono- crotaline. XIV. Synthesis of monocrotalic acid. }. Am. Chem. Soc., 74:5608-11. With P. R. Shafer and B. H. Braun. The structure of monocro- taline. XV. I. Am. Chem. Soc., 74:5612- 15. With B. H. Braun. Quinone imides. XXII. The reaction of primary aromatic amines with 2,3,5,6-tetrachloro1-quinonedibenzene- sulfonimide. }. Am. Chem. Soc., 74:5869-71. With D. S. Acker. Quinone imides. XXIII. Addition reactions of p-quinonedibenzimide and related compounds. }. Am. Chem. Soc., 74:5872-76. With I. M. Stewart. Quinone imides. XXIV. o-Quinonemono- imides. I. Am. Chem. Soc., 74:5876-80. 1953 With E. F. Elslager and T. E. Young. Quinone imides. XXV. Addi- tion of mercaptans to p-quinonedibenzenesulfonimide. I Am. Chem. Soc., 75:663-66. With P. R. Shafer. Quinone imides. XXVI. Adducts of p- quinonebis~dimethylaminosulfonimides) and their hydrolysis products. I. Am. Chem. Soc., 75:667-70. With D. C. Blomstrom. Restricted rotation in aryl amines. XV. Stereoisomeric diglutarimidomesitylenes. I. Am. Chem. Soc., 75:2375-77. With B. L. Van Duuren. Dicrotaline. The structure and synthesis of dicrotalic acid. }. Am. Chem. Soc., 75:2377-79. With T. E. Young. Quinone imides. XXVII. Addition reactions of substituted p-quinonedibenzenesulfonimides. I Am. Chem. Soc., 75:3235-39. With D. C. Blomstrom. Quinone imides. XXVIII. Addition of ac- tive methylene compounds to p-quinonedibenzenesulfonimide and its derivatives. J. Am. Chem. Soc., 75:3403-5. With D. C. Blomstrom. Quinone imides. XXIX. Addition of hydra- zoic acid and phenols top-quinonedibenzenesulfonimide and its derivatives. }. Am. Chem. Soc., 75:3405-8. Uber die Chemie der Senecio-Alkaloide und verwandter Verbin- dungen. Angew. Chem., 65:433-42. With B. L. Van Duuren. Usaramoensine, the alkaloid in Crotalaria usaramoensis E. G. Baker. Integerrimine from Crotalaria incana

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ROGER ADAMS 43 Linn and senecionine from Senecio globellus D. C. Stereochemical relationships. I. Am. Chem. Soc., 75:4631-35. With B. L. Van Duuren. Structure of heliotrinic acid. I. Am. Chem. Soc., 75:4636-38. With B. L. Van Duuren. Riddelliine, the alkaloid from Senecio rid- delii. II. Structure of riddellic acid and total structure of riddel- liine. l. Am. Chem. Soc., 75:4638~2. With B. H. Braun and S. H. Pomerantz. Quinone imides. XXX. Addition of primary and secondary aromatic amines. I. Am. Chem. Soc., 75:4642-44. With R. R. Holmes and }. W. Way. Quinone imides. XXXI. 3,3-Dimethoxydiphenoquinonedibenzenesulfonimide and its reaction products. I. Am. Chem. Soc., 75:5901-4. 1954 With S. H. Pomerantz. Quinone imides. XXXII. Reactions of 1,4-naphthoquinonedibenzenesulfonimide with pyridine and its derivatives. }. Am. Chem. Soc., 76:702-6. With T. E. Young and R. W. P. Short. Quinone imides. XXXIII. Orientation of adducts from 2-benzenesulfonyl1-quinonedi- benzenesulfonimide. I. Am. Chem. Soc., 76: 1114-18. With I. }. Pachter. The action of alkali on bromopyridopyri- midones. J. Am. Chem. Soc., 76:1845-47. With R. W. P. Short. Quinone imides. XXXIV. Addition of dienes to substituted p-quinonedibenzenesulfonimides. J. Am. Chem. Soc., 76:2408-10. With I. W. Way. Quinone imides. XXXV. o-Quinonedibenzimides. I. Am. Chem. Soc., 76:2763-69. With S. Miyano. 2-Aminopyridine 1-oxides. J. Am. Chem. Soc., 76:2785-86. With S. Miyano. Condensation reactions of picoline 1-oxides. Am. Chem. Soc., 76:3168-71. J With R. S. Colgrove. Quinone imides. XXXVI. Orientation of groups in adducts of quinone diimides with different N- substituents. J. Am. Chem. Soc., 76:3584-87. With R. H. Mattson. Restricted rotation in aryl amines. XVI. 4-Substituted 1-amino-2-methylnaphthalenes. J. Am. Chem. Soc., 76:4925-28. With K. V. Y. Sundstrom. Restricted rotation in aryl amines. XVII. Effect of varying the 4-substituent on the stability of optically

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44 BIOGRAPHICAL MEMOIRS active N-benzenesulfonyl-N-carboxymethyl- 1-amino-2-methyl- naphthalene. }. Am. Chem. Soc., 76:547~77. With D. C. Blomstrom and K. V. Y. Sundstrom. Restricted rotation in aryl amines. XVIII. Resolution of N-carboxymethyl-N- methyl-3-bromomesidine. }. Am. Chem. Soc., 76:5478-79. With B. L. Van Duuren. Stereochemistry of the pyrrolizidine bases. I. Am. Chem. Soc., 76:6379-83. 1955 With W. P. Samuels, Jr. Quinone imides. XXXVII. Conversion of p-quinone diimides to indoles. }. Am. Chem. Soc., 77:5375-82. With W. P. Samuels, Jr. Quinone imides. XXXVIII. Adducts to p-quinonedimethanesulfonimide and their hydrolysis products. }. Am. Chem. Soc., 77:5383-85. With E. I. Agnello and R. S. Colgrove. Quinol imides and o-quinone imide diacetates. I. Conversion of 4-benzenesulfonamidotri- phenylmethane to 4-benzohydryl - -quinonediacetatebenzene- sulfonimide. }. Am. Chem. Soc., 77:5617-25. 1956 With M. Gianturco. Senecio alkaloids. The corr~position of"hieraci- foline" and "jacobine." }. Am. Chem. Soc., 78:398-400. With L. Whitaker. Quinone imides. XXXIX. Adducts of quinone monoimides and conversion of active methylene adducts to ben- zofurans. }. Am. Chem. Soc., 78:658-62. With K. R. grower. Restricted rotation in aryl amines. XVIII. Ef- fect of remote substituents on the stability of optically active N-benzenesulfonyl-N-carboxymethyl-3-benzylmesidine. l. Am. Chem. Soc., 78:663-66. With M. Gianturco. The alkaloids of Crotalariajuncea. J. Am. Chem. Soc., 78:1919-21. With M. Gianturco. Senecio alkaloids. Structure of trichodesmine. }. Am. Chem. Soc., 78:1922-25. With M. Gianturco. Crotalaria alkaloids. The structure of junceine. I. Am. Chem. Soc., 78:1926-28. With M. Gianturco and B. L. Van Duuren. The alkaloids from Senecio tomentosus. Observations on the alkaloid jacobine and on the structure of jaconecic acid. I Am. Chem. Soc., 78:3513- 19.

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ROGER ADAMS 45 With W. Reifschneider. Addition of phenylmagnesium bromide to aliphatic conjugated dibenzenesulfonimides. l. Am. Chem. Soc., 78:3825-28. With M. Gianturco. The structures of grantianine and sceleratine. A suggested biogenesis of the acids in alkaloids from Senecio and Crotalaria species. I. Am. Chem. Soc., 78:4458~4. With K. R. grower. Quinol imide acetates. 2,4,6-Trimethyl - - quinobenzenesulfonimide acetate and 2,4-dimethyl-o-quinol- benzenesulfonimide acetate. {. Am. Chem. Soc., 78:4770-73. With I. E. Dunbar. Quinol imide acetates. III. Addition reactions of 2-methyl - -naphthoquinoll-toluenesulfonimide acetate. I. Am. Chem. Soc., 78:4774-78. With M. Gianturco. Senecio alkaloids: the alkaloids of Senecio brasil- iens?s, fremonti and ambrosioides. J. Am. Chem. Soc., 78:5315-17. With M. D. Nair. Quinone imides. XL. Orientation in addition of hydrogen chloride to 2-substituted p-quinonedibenzimides. I. Am. Chem. Soc., 78:5927-31. With M. D. Nair. Quinone imides. XLI. Orientation in addition of thiophenol and benzenesulfinic acid to 2-substituted p-qui- nonedibenzimides. l. Am. Chem. Soc., 78:5932-38. 1957 With M. Gianturco. Senecio alkaloids: mikanoidine, the alkaloid from Senecio mikanoides. ]. Am. Chem. Soc., 79: 166 69. With H. H. Gibbs. Restricted rotation in aryl amines. XIX. Effect of substituents in the 4-position on the optical stability of 1-amino-2-methylnaphthalene derivatives. J. Am. Chem. Soc., 79: 170-73. With M. Gianturco. Senecio alkaloids: spartioidine, the alkaloid from Senecio spartioides; stereochemical relationship to other Senecio alkaloids. I. Am. Chem. Soc., 79:174-77. With M. D. Nair. Quinone imides. XLII. Orientation of adducts from substituted p-quinonedimethanesulfonimides. I. Am. Chem. Soc., 79:177-79. With E. L. DeYoung. Quinone imides. XLIII. The reactions of o-quinonedibenzenesulfonimides. J. Am. Chem. Soc., 79: 417-19. With E. L. DeYoung. Quinol imide acetates. IV. The reactions of 2,4-dimethyl - -naphthoquinol1-toluenesulfonimide acetate. I. Am. Chem. Soc., 79:705-8.

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46 BIOGRAPHICAL MEMOIRS With W. Reifschneider. The reaction of 2-bromopyridine N-oxides with active methylene compounds. {. Am. Chem. Soc., 79: 223~39. With H. I. Neumiller, fir. Quinone imides. XLIV. The orientation of groups in addition reactions to substituted p-quinonedi- benzimides. I. Am. Chem. Soc., 79:3808-12. With M. I. Gortatowski. Restricted rotation in arylamines. XX. Ef- fect of meta substitution on the optical stability of some N- benzenesulfonyl-N-carboxymethylmesidines. I. Am. Chem. Soc., 79:5525-28. 1958 With L. M. Werbel and M. D. Nair. Quinone imides. XLVI. Addi- tion of heterocyclic active methylene compounds to p-benzo- quinone diimides. I. Am. Chem. Soc., 80:3291-93. With I. E. Dunbar. Restricted rotation in arylamines. XXII. N- benzenesulfonyl-N-carboxymethyl-3-amino-2,4,6-trimethylpyri- dine and its N-oxide. I. Am. Chem. Soc., 80:3649-51. With I. S. Dix. Restricted rotation in arylamines. XXI. Effect of 3-substituents on the optical stability of some N-benzene- sulfonyl-N-carboxymethylmesidines. I. Am. Chem. Soc., 80: 4579-81. With I. S. Dix. Reaction of 2-aminopyridine with a-haloketones. J. Am. Chem. Soc., 80:4618-20. With L. M. Werbel. Preparation of quinol imide acetates. VI ~ Scope and limitations. I. Am. Chem. Soc., 80:5799-803. 1959 With W. Reifschneider. A synthesis of 6-hydroxy-4-quinolizones. I. Am. Chem. Soc., 81:2537-41. With A. Ferretti. Thioethers from halogen compounds and cu- prous mercaptides. II. {. Am. Chem. Soc., 81:4927-31. With A. Ferretti. Thioethers. III. Preparation of aromatic di- and tri-mercapto compounds by dealkylation off aryl alkyl thio- ethers. I. Am. Chem. Soc., 81:4939-40. With D. Fles. The absolute configuration of the Cat atom in retrone- canone ~ 1-methyl-7-oxopyrrolizidine). J. Am. Chem. Soc., 81 :494~51. With D. Fles. The absolute configuration of the Cal atom in pyrro-

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ROGER ADAMS 47 lizidine moieties of Senecio alkaloids. T Am. Chem. Soc.. 81 :5803-5. With C. C. I. Culvenor, C. N. Robinson, and H. A. Stingl. Synthesis of heliotramide. Aust. T. Chem., 12: 70~ 11. 1960 With S. Miyano and D. Fles. 1-Hydroxypyrrolizidine and related compounds. I. Am. Chem. Soc., 82:146~68. With M. D. Nair. Stereochemistry of necic acids. }. Am. Chem. Soc., 82:378~87. With T. A. Geissmann and J. D. Edwards. Gossypol, a pigment of cottonseed. Chem. Rev., 60:555-74. 1961 With M. D. Nair. The structure of riddellic acid and the stereo- chemistry of necic acids. ]. Am. Chem. Soc., 83:922-26. With A. Ferretti. Restricted rotation in aryl amines. XXII. Effect of meta substitution on the optical stability of some N-benzene- sulfonyl-N-carboxymethylmesidines. I Am. Chem. Soc., 83: 2559-63. With S. Miyano and M. D. Nair. Synthesis of substituted pyrro- lidines and pyrrolizidines. ]. Am. Chem. Soc., 83:3323-27. With M. D. Nair. Benzimidazole syntheses by oxidative cyclization with peroxytrifluoroacetic acid. I. Am. Chem. Soc.,83:3518-21.