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RICHARD BALDWIN TURNER October 7, 1916-December 22, 1971 BY MARSHALL GATES RICHARD B. TURNER was born in Minneapolis, Minnesota on October 7' 1916 to Hubert Michael Turner ant! Jessie Baldwin Turner, both highly cultured people and edu- cators. Their son's entire life and career reflected this heri- tage. Hubert Turner was born in 1882 in HilIsboro, Illinois. After graduating from the University of TIlinois in 1910, he stayed on as an assistant instructor for two years while taking graduate work in mathematics, physics, and electrical engi- neering. Here he met Jessie Baldwin, a teacher and graduate of the university in botany. They were married in ~ 9 ~ 2 while both were members of the faculty of the university. After an interlude in Minneapolis, where Dick was born, the family moved to New Haven in lL918 where Hubert Tur- ner took up an appointment as assistant professor of electri- cal engineering at the Sheffield Scientific School at Yale. His entire subsequent career was spent at Yale; he became inter- nationally known in the field of electrical communication engineering. He was a member of the American Institute of Electrical Engineers, the International Union of Scientific Radio Telegraphy, the Franklin Institute, the Institute of Raclio Engineers, the American Standards Association, and the American Association for the Advancement of Science. 351

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352 BIOGRAPHICAL MEMOIRS He retired from Yale in 1952 anct cTiect of a heart attack while living at the Yale Faculty Club in 1965. Dick's mother, Jessie Baldwin Turner, was born in Deer Park, Illinois. She maintained her interest in botany in New Haven, where she was a member of the Fern Society ant! had a collection of over one hunctrect varieties of ferns. Both parents collected rocks, shells, and stamps ant! were evict bird watchers. They were widely react and well informed, of high principles, interested in both worIct ant! local affairs, and maintained a home in which intellectual values were fostered. Dick's only sibling, Elizabeth, stied at age nine, and he was raised as an only chitct from then on. He spent all his chilcI- hood in New Haven, strongly influenced by his parents and the college community. He attencled Susan Sheridan Junior High School and New Haven High School, graduating in 1933. He was a bright ant! inquisitive chilcI, excelling in mathematics, physics, and chemistry. Both parents supple- mentect and enriched his formal education by tutoring him at home. Turner was also a talentec! musician ant! cluring these years playecl the piano, clarinet, and trombone. This talent for and love of music was to remain with him all his life; he particularly enjoyed Dixieland jazz and was aclept in this style with the clarinet. While at Harvard he played in the college banct. Like most boys of his age, he was keenly interested in athletics, and he also enjoyed sailing ant! woodworking. In later years he found time to combine the last two avocations, building a sailboat that he ant! his family greatly enjoyed! using. He was also an evict reacler, particularly in history, and was ectitor-in-chief of his school newspaper, The Sentinel, his . . - ~un~or ant senior years. In ~ 934 Turner entered Harvard, graduating in ~ 938. He remained at Harvarc! for graduate studies, first uncler Wil- liam F. Ross, then with Louis F. Fieser, uncler whom he com-

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RICHARD BALDWIN TURNER 353 pleted his Ph.D. in 1942. He remained at Harvarc! for another year working under a National Defense Research Committee contract, then went to the Mayo Clinic in 1943 to work with the group assembled by E. C. Kendall to examine the chemistry of the adrenocorticosteroicis. After two years at the Mayo Clinic, Turner in 1945 joined a synthetic group at MIT carrying on a wartime project on the synthesis of antima- larials under the ctirection of Arthur C. Cope. He remained with this group until 1948, when he returned to Harvard as a research fellow of the American Cancer Society, for the first time working alone or with one or two technicians on prob- lems of his own inception. He remained there until the fall of 195 I, when he took a position as assistant professor of chem- istry at Rice University, rising through the academic ranks to associate professor (1953) and professor (1956~. He re- mainect at Rice for the rest of his career. In 1952 Turner married Halina Deschko, a native of the Ukraine who had come to this country after World War IT. She had graduated from Mt. Holyoke and the Simmons Col- lege School of Social Work. They tract three children: Richard, Jr., Tamara, and William. Richard, fir., is an archi- tect and his younger brother, William, is also entering this fielct; Tamara's professional interests lie in anthropology. Turner was a devoted husband! ant! father and spent much time with his family in spite of the heavy demands of his professional career. Turner was an unusually able teacher and lecturer. His presentations, both in the classroom anc! at symposia anc! meetings, were sharp, incisive, rigorous, and polished, and he was invited to present his work widely both here ant! abroad. THE SCIENTIFIC WORK OF R. B. TURNER Aside from the work he carrier! out for his Ph.D., Richard Turner's first significant contribution to chemistry came

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354 BIOGRAPHICAL MEMOIRS from the two years he spent with Kendall's group at the Mayo Clinic. A series of six papers on the general subject of steroids derived from bile acids appeared in the period from 1946 to 1952. Using ~9'~ choleric acid as a raw material, efficient methods were developed for the preparation of the impor- tant ~ I-ketocholanic acid and a number of its close relatives ant! the subsequent degradation of ~ I-ketocholanic acid to Il-ketoetiocholanic acid! by removal of the bile acid sicle chain. This work was crucial for the preparation of the first partially synthetic samples of Kendall's compound A for clini- cal trials. During the course of this work, stereochemical as- signments were macle to twenty-five bile acid derivatives substituted in ring C. Turner's interest in steroids ant! relates! compounds en- clured in somewhat modified form throughout his career. He was the first to synthesize C~4 labeled cholestenone and testos- terone ~ ~ 947), and sporadic publications on a variety of prob- lems related to steroids appeared from then until 1960. During the period from 1954 to 195S, Turner ant! his co- workers carried out structural studies on the carcliotonic ste- roicI ouabagenin, derived from the glycoside ouabain long user! as an arrow poison by the East African Somalis. They were able to locate the remaining uncertain hyciroxyl group at C ~ ~ and were able to correlate ouabagenin and strephan- thidine, another carcliotonic aglycone, by conversion of both to a common derivative still retaining the hydroxyl group at CI4 and the butanolide ring. A general interest in the structure and synthesis of natural substances, of which the above work in the steroid field was one manifestation, continued to occupy Turner throughout most of his career. Determination of the structure and com- pletion of a synthesis of cassaic acid ant! a synthesis of phyllo- cIaden were published in the perioc! from 1959 to 1966, and he and his coworkers had begun a synthetic approach to the

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RICHARD BALDWIN TURNER 355 diterpenoid alkaloids at about this time. At the time of his cleath, Turner and his coworkers were at work on a synthesis of marasmic acid! and hac! completed construction of the carbon skeleton in its correct stereochemical form. Various syntheses of intermediates used in the extensive antimalarial program carried out (luring the later stages of WorIcl War 11[ comprise the work Turner carried out while in the group heaciecl by Arthur C. Cope in the period from 1945 to 1948. Synthetic work in the naphthoquinone field with Louis F. Fieser formed the subject of his cloctoral dissertation as well; these results were publisher! in 1947. In a penetrating and important early paper, Turner, in collaboration with Dorothy VoitIe, established the structure of ~~-~-acetyI-2-methy~cyclohexene as the s-cis conformer; this was done by a study of its uv absorption ant! that of a number of more rigid! a,,B-unsaturated ketones and provider! an explanation of the lowered extinction coefficients in such substances. Turner's bibliography contains contributions on a wide variety of subjects (synthesis, structures of natural products, use of radioactive carbon in labeling important hormones, confirmational analysis, instrumental methods as probes of structure, stereochemistry, ant! such diverse biochemical sub- jects as the mechanism of uptake of radioactive iodine by thyroid tissue and the biochemistry of alclosterone), but by far the most important contribution he and his colleagues maple was their use of heats of hydrogenation as a too! to study a variety of problems having to do with the comparative stabilities of a wide variety of olefins, estimates of strain ener- gies ant! conjugative interactions, confirmational problems, and others. This work brought order based on quantitative results to a large and important area of organic chemistry that theretofore had been characterized by conjecture, hy- pothesis, and speculation. .

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356 BIOGRAPHICAL MEMOIRS It is perhaps inappropriate to review this work in detail here, but the following important results and conclusions arose directly from it: The question of homoallylic resonance in such sub- stances as norbornadiene, barrelene, and cis, cis, cis-11,4,7- cyclononatriene was resolved once and for all. They are de- void of such resonance. The relative stabilities of various double-bond isomers of cholestene were established on a quantitative basis (~2 is the most stable). The relative stabilities of cis and bans . Isomers of cy- clooctene, cyclononene, and cycloclecene were quantitatively cleterminect. In any given pair, the cis isomer is more stable, cas-cyclodecene having the lowest enthalpy of hydrogenation of any alkene examined. Reliable values for the stabilization energies of a number of theoretically important cyclic polyenes were estab- lished. Among those studied were cyclooctatetrene; I,3,5- cyclooctatriene; azulene; heptafuIvene; heptafuIvalene and its dihydro derivative, tropone pleiaclylene. tropylium ion; and ace- The relative stabilities of exo and undo olefins in five-, six-, and seven-membered ring systems were cletermine~l. In all cases, the enclo isomer is the more stable. There tract been claims, albeit somewhat ambiguous, that couIct have been interpreted as indicating a greater stability for the exo isomer in five-membered rings. The order of stability for substituted olefins was estab- lished unambiguously. This work also showed the impor- tance of planarity for olefin stability; cis-di-t-butylethylene has the highest enthalpy of hydrogenation of any simple olefin examined, nearly 10 kcal/mole higher than its bans isomer.

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RICHARD BALDWIN TURNER 357 The essential correctness of a single most stable confor- mation for cyclociecane, suggested by Dunitz, was established by the demonstration of the necessity for a transoid confor- mation in I, I,4,4-tetramethy~cyclodecen-7. The well-known stabilizing effect of alky! groups on carbon-carbon double-bonds was shown to be independent of the nature of the alkyd group and therefore not readily accounted for on steric grounds. The strain energies of a number of theoretically in- . . ~ teresting small ring compounds were determined. I,3- Dimethy~bicyclof I. I.0] butane has the remarkably high value of 67 kcaVmole. The conjugative stabilization in 2-methyI-l,3,5-hexa- triene was shown not to be the result of strengthening of sp2-sp2 bonds relative to sp3-sp2 bonds, but to be consistent with the resonance hypothesis. By inference, this finding should also apply to I,3-butadiene ant! I,3,5-hexatriene and similar substances. The triple-bone! strain in cyclic alkynes was cletermined. It is large in cyclooctyne, about 2.9 kcaVmole in cyclononyne and negligible in ten- ant! tweIve-membered rings. Reliable quantitative evidence on strain and conjugative interactions in such substances as the cyclohexaclienes and the cycloheptaclienes, as well as in the cyclooctatrienes, was provident. These data will have to be taken into account in any discussion of such meclium-size ring systems. Quantitative evidence for transannular interactions in medium-size rings, both saturated and unsaturated, was ac- cumulated. In this large and important field Turner perceived the need for reliable quantitative data, selected the substrates to be examined with a keen eye for the significance of the f~nd- ings, provided the methodology for obtaining them, mea-

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358 BIOGRAPHICAL MEMOIRS sured the quantities with precision, and interpreted the re- sults with rigor and sophistication. The importance of this work as a whole attracted much attention, and led to fruitful collaboration with other well- known chemists both here and abroad. The most extensive such collaboration was between Turner and William von E. Doering. They and their collaborators published five joint papers. Finally, it is remarkable that nearly 20 percent of Turner's papers were published under his name alone. He was a gifted experimentalist and enjoyed laboratory work. He continued to carry on experimentation with his own hands right up to the time of his death.

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RICHARD BALDWIN TURNER BIBLIOGRAPHY 1941 359 With W. F. Ross. Hemo-globin linkage of hemoglobin. II. Analysis of the CO product. The pancreatic digestions of several forms of hemoglobin. I. Biol. Chem., 139:603-10. 1946 With V. R. Mattox, L. L. Engel, B. F. McKenzie, and E. C. Kendall. Steroids derived from bile acids. III. Derivatives of /\9 ii cho- lenic acid with substituents at C3 and Cot. }. Biol. Chem., 162:571-84. With V. R. Mattox, L. L. Engel, B. F. McKenzie, W. F. McGuckin, and E. C. Kendall. Steroids derived from bile acids. IV. 3,9-Epoxy-/\ choleric acid and closely related compounds. I. Biol. Chem., 164: 569-96. With V. R. Mattox, L. L. Engel, B. F. McKenzie, and E. C. Kendall. Steroids derived from bile acids. V. Introduction of oxygen at Cal. I. Biol. Chem., 166:34~65. With A. C. Cope. ~x(Dialkylaminomethyl)-2-phenyl-4-quinoline- methanols with 8-amino or hydroxy substituents. I. Am. Chem. Soc., 68:221~19. With }. Mills and A. C. Cope. c~(Dialkylaminomethyl)-8-amino (or hydroxy)-4-quino-linemethanols. I. Am. Chem. Soc., 68: 222() 24. 1947 Radioactive cholestenone. I. Am. Chem. Soc., 69:72~27. Radioactive testosterone. Science, 106:248. With L. F. Fieser. Addition of mercapto derivatives to 2-methyl- 1,4-naphthoquinone. I. Am. Chem. Soc., 69:233~38. With L. F. Fieser. Naphthoquinone acids and ketols. I. Am. Chem. Soc., 69:2338-41. 1948 Structure and synthesis of cardiac genies. Chem. Rev., 43:1-42. With V. R. Mattox, B. F. McKenzie, L. L. Engel, and E. C. Kendall. Steroids derived from bile acid. VII. Probable stereochemical configuration of some derivatives of the bile acids. I. Biol. Chem., 173:283-94.

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360 BIOGRAPHICAL MEMOIRS 1949 With A. C. Cope, H. R. Nace, W. R. Hatchard, W. H. Jones, and M. A. Stahmann. Synthesis of 6-methoxy-8-amino-quinoline de- rivatives. Ethylenimine rearrangements in attachment of monoalkylamino-alkyl side chains. I. Am. Chem. Soc., 7 1: 554 61. 1950 Steroids labeled with isotopic carbon: Cholestenone and testos- terone. I. Am. Chem. Soc., 72:57~85. With D. M. Voitle. Preparation of D~-cysteine hydrochloride. I. Am. Chem. Soc., 72:628-29. Stereochemistry of the peracid oxidation of ketones. l. Am. Chem. Soc., 72:878-82. With D. M. Voitle. Reaction of 1-acetyl-2-methylcyclohexene with cyclohexanone. T. Am. Chem. Soc., 72:416~68. 1951 With D. M. Voitle. The structure of 1-acetyl-2-methylcyclohexene; Spectral characteristics of s-cas- OCR for page 350
RICHARD BALDWIN TURNER 1953 361 With R. B. Woodward. Chemistry of the cinchona alkaloids. In: The Alkaloids Chemistry and Physiology, vol. 3, p. 1. New York: Aca- demic Press. Stereospecificity in the rearrangement of 17-hydroxy-20-oxo ste- roids. I. Am. Chem. Soc., 75:348~88. With R. P. A. Sneeden. Ouabagenin. I. The relationship between ouabagenin monoacetonide and anhydroouabagenin. I. Am. Chem. Soc., 75:3510-13. Acylation of 17-hydroxy-20-oxo-steroids. I. Am. Chem. Soc., 75: 3489-92. With H. R. Nace. Dipole moments and conformations of androstane-3,17-dione and of etiocholane-3,17-dione. I. Am. Chem. Soc., 75:4063-66. Infrared absorption of some steroid digitonides. I. Am. Chem. Soc., 75:4362-63. Molecular rotation differences for 17-hydroxy-20-keto steroids. I. Am. Chem. Soc., 75:3604-5. 1954 With R. P. A. Sneeden. Structure of ouabagenin. Chem. Ind., 1954: 1235-36. With H. I. Nachimson, R. H. Benson, I. I. Szafir, H. C. Allen, Jr., and R. V. Talmage. Comparative study of effects of phenothia- zine and iodine on thyroid uptake of iodine. Proc. Soc. Exp. Biol. Med., 87:157-62. Pyrolysis of the Windaus acid. I. Am. Chem. Soc., 76: 1390. 1955 With R. P. A. Sneeden. Ouabagenin. II. The hydroxyl groups of the A/B ring system. {. Am. Chem. Soc., 77:130-34. With R. P. A. Sneeden. Catalytic dehydrogenation of primary and secondary alcohols with platinum and oxygen: Selective dehy- drogenation in the steroid series. I. Am. Chem. Soc., 77: 190-91. With R. Anliker. Stereochemistry of the epimeric 17c`-methyl-D- homo-testosterones. Helv. Chim. Acta, 38:411-20. 1956 With R. V. Talmage, R. H. Benson, I. I. Szafir, and H. C. Allen. Excess iodide as the primary cause of the inhibition of thyroid

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362 BIOGRAPHICAL MEMOIRS uptake of radioiodine produced by phenothiazine N. F. (green). I. Am. Vet. Med. Assoc., 128: 150~51. With I. A. Meschino. Location of the sixth hydroxyl group in oua- bagenin. I. Am. Chem. Soc., 78:5130-31. With D. E. Nettleton, Jr., and R. Ferebee. Synthetic routes to 3,6-dimethoxyphenanthrene. I. Am. Chem. Soc., 78:5923-27. 1957 With R. L. Anliker, A. S. Lindsey, and D. E. Nettleton, Jr. A syn- thetic approach to polycyclic hydroaromatic systems related to the 19-nonsteroids. I. Am. Chem. Soc., 79:220-26. With R. H. Garner. Stability relation of 1-methylcyclopentene and methylenecyclopentane. I. Am. Chem. Soc., 79:253. With M. Perelman and K. T. Park, fir. Tracer studies in rearrange- ments of 17-hydroxy-20-oxosteroids and observations on the reaction of compound ~ monoacetate with Al isopropoxide. J. Am. Chem. Soc., 79:1108-14. With W. R. Meador and R. E. Winkler. Heats of hydrogenation. I. Apparatus and the heats of hydrogenation of bicyclo[2.2.1]hep- tadiene bicyclof2.2.2joctane and bicyclo[2.2.2]octadiene. i. Am. Chem. Soc., 79:4116-21. With W. R. Meador and R. E. Winkler. Heats of hydrogenation. II. Heats of hydrogenation and the acid catalyzed isomerization of unsaturated steroids. I. Am. Chem. Soc., 79:4122-27. With W. R. Meador, W. v. E. Doering, L. H. Knox, I. R. Mayer, and D. W. Wiley. Heats of hydrogenation. III. Hydrogenation of cycloocta tetraene and of seven-membered nonbenzenoid aro- matic compounds. I. Am. Chem. Soc., 79:4127-33. With W. R. Meador. Heats of hydrogenation. IV. Hydrogenation of cats and tra7's-cycloolefins. J. Am. Chem. Soc., 79:4133-36. , ,~ 1958 With R. H. Garner. Heats of hydrogenation. V. Relative stabilities in exocyclic endocyclic olefin pairs. J. Am. Chem. Soc., 80: 1424-30. With D. E. Nettleton, fir., and M. Perelman. Heats of hydrogena- tion. VI. Substituted ethylene. I. Am. Chem. Soc., 80: 1430-33. With J. A. Meschino. Ouabagenin. III. Assignment of the sixth hydroxyl group and a structural correlation with strophanthi- din. J. Am. Chem. Soc., 80:4862-65.

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RICHARD BALDWIN TURNER 1959 363 Stabilization and strain energies from heats of hydrogenation. Ke- kule Symposium on Theoretical Organic Chemistry, London, 1958. In: Theoretical Organic Chemistry, p. 67. London: Butter- worths Scientific Publications. With E. G. Herzog, K. B. Morin, and A. Riebel. Structure of cassaic acid. Tetrahedron Lett., 1959, 2: 7-10. Thermal evidence for hyperconjugation. Tetrahedron, 5:127-34. 1960 With P. E. Shawl Total synthesis of a degradation product of phyl- locladene. Tetrahedron Lett., 18:2~27. With H. R. Nace. Dipole moments of androstan- 17-one, testan- 11- one, and testane-11,17-dione. I. Org. Chem., 25:1403-4. With H. Prinzbach and W. v. E. Doering. Heats of hydrogenation. VII. Cycloheptatrienylium~tropylium) ion. J. Am. Chem. Soc., 82:3451-54. With R. H. Benson. Acetyl group determination using acetic an- hydride Ci4. Anal. Chem., 32:1464-65. 1961 With R. E. Lee and E. G. Hildenbrand. Trans-decalin-2,9- dicarboxylic acid and related derivatives. I. Org. Chem., 26:4800~803. With K. H. Ganshirt. Total synthesis of phyllocladene. Tetra- hedron Lett., 1961, 231-33. 1964 With P. Goebel, l. Sicher, and M. Svoboda. Conformation of un- saturated cyclodecane derivatives. Enthalpy of hydrogenation of alkylcyclodecenes and -cyclodecynes. Proc. Chem. Soc. Lon- don (July):237-38. With W. R. Roth, W. B. Bang, P. Goebel, R. L. Sass, and A. P. Yue. Question of homoconjugation in As, As, cas-1,4,7-cyclonona- triene. J. Am. Chem. Soc., 86~15~:3178-79. Heat of hydrogenation of bicyclof2.2.2]octa-2,5,7-triene. I. Am. Chem. Soc., 86~17~:3586-87. With P. Grafen. 1-Cyano-5-methoxy-2-tetralone. Tetrahedron Lett., 52:3935-37.

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364 BIOGRAPHICAL MEMOIRS 1965 With P. Goebel, W. v. E. Doering, and I. F. Coburn. Strain in 1,3-dimethylbicyclof 1,1,0]butane. Tetrahedron Lett., 1965, 997-1002. 1966 With I. Sicher, M. Svoboda, I. Zavada, and P. Goebel. Stereo- chemical studies. Part 36. An approach to conformational analy- sis of medium ring compounds, unsaturated 10-membered ring derivatives. Tetrahedron, 22:659-71. With O. Buchardt, E. Herzog, R. B. Morin, A. Riekl, and I. M. Sanders. Structure and total synthesis of cassaic acid. I. Am. Chem. Soc., 88:1766-75. With K. W. Ganshirt, P. E. Shaw, and I. D. Tauter. Total synthesis of phyllocladene. J. Am. Chem. Soc., 88: 1776-85. With G. D. Diana, G. E. Fodor, K. Gebert, D. L. Simmons, A. S. Rao O. Roos, and W. Wirth. Synthetic intermediates related to diterpene alkaloid. I. Am. Chem. Soc., 88:1786-92. 1968 With I. Sicher, M. Svoboda, and B. I. Mallon. Stereochemical stud- ies. 47. Conformational analysis of many-membered ring com- pounds. Cyclododecenes. }. Chem. Soc., 1968B:441~7. With R. D. Stipanovic. Cyclohexenone-4-acetic acid derivatives from the addition of diazoacetic ester to beta, gamma unsatu- rated ketals. J. Org. Chem., 33:3261-63. With P. Goebel, B. I. Mallon, W. v. E. Doering, I. F. Coburn, and M. Pomerant. Heats of hydrogenation. VIII. Compounds with 3- and 4-membered rings. I. Am. Chem. Soc., 90:4315-22. With R. B. Miller and I. L. Lin. Stereochemical investigations of methyl epimerization in derivatives of 1-methyl-trans-decalin. J. Am. Chem. Soc., 90:612~30. With P. Grafen, H. I. Kabbe, O. Roos, G. D. Diana, and T. T. Li. Synthetic approaches to diterpene alkaloids. I. Am. Chem. Soc., 90:6131-35. With P. M. Lesko. Strain energy in bicyclof3,3,1]non-1-ene. J. Am. Chem. Soc., 90:688~89.

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RICHARD BALDWIN TURNER 365 1970 With M. Tichy. Heats of hydrogenation of c~s-2-methylhexatriene and trans-2-methylhexatriene resonance or sigma bond energy. Proc. Natl. Acad. Sci. USA, 67~4~:12A. With L. P. Cawley, S. C. Sommers, and R. Horton. Biochemistry and physiology of aldosterone. Am. I. Clin. Pathol., 54:311-13. Chemical properties of aldosterone. Am. I. Clin. Pathol., 54 28~96. 1971 With A. Meyer. Interesting synthesis of 3-methoxy-2,6-dimethyl- phenethyl alcohol. Tetrahedron, 27:2609-15. With V. Boekelheide and W. S. Lindsay. Heats of hydrogenation. Acepleiadylene. Tetrahedron, 27(151:3341~4. 1973 With P. Goebel, B. I. Mallon, and A. D. Barrett. Heats of hydro- genation. IX. Cyclic acetylenes and some miscellaneous olefins. I. Am. Chem. Soc., 95:790-92. With S. R. Wilson. Pyrazoline stereochemistry. Use of nuclear magnetic resonance shift reagents with azo-compounds. J. Chem. Soc. Chem. Commun., 1973:557-58. With S. R. Wilson. Studies in sequiterpene synthesis. Marasmic acid skeleton. J. Org. Chem., 38:2870-73. With B. J. Mallon, M. Tichy, W. v. E. Doering, W. R. Roth, and G. Schroder. Heats of hydrogenation. X. Conjugative interaction in cyclic dienes and trienes. I. Am. Chem. Soc., 95:8605-10.