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OCR for page 1
Biographical :7Vfemoirs
VOLUME 53
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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 sisters—tall, 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 catalyst—discovered 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.
OCR for page 10
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
OCR for page 11
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.
OCR for page 38
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.
OCR for page 39
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.
OCR for page 40
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.
OCR for page 41
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.
OCR for page 42
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
OCR for page 43
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
OCR for page 44
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.
OCR for page 45
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.
OCR for page 46
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-
OCR for page 47
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.
