James McCue Bobbitt (January 18, 1930 – November 22, 2021) was an American chemist and academic who taught chemistry at the

University of Connecticut The University of Connecticut (UConn) is a public land-grant research university in Storrs, Connecticut, a village in the town of Mansfield. The primary 4,400-acre (17.8 km2) campus is in Storrs, approximately a half hour's drive from Hart ...

from 1956 to 1991 and developed the Bobbitt reaction.

Early life and education

Bobbitt was born on January 18, 1930, in

Charleston, West Virginia Charleston is the capital and List of cities in West Virginia, most populous city of West Virginia. Located at the confluence of the Elk River (West Virginia), Elk and Kanawha River, Kanawha rivers, the city had a population of 48,864 at the 20 ...

, to parents James Sterling Bobbitt and Grace McCue Bobbitt. He earned a Bachelor of Science degree in chemistry from

West Virginia University West Virginia University (WVU) is a public land-grant research university with its main campus in Morgantown, West Virginia. Its other campuses are those of the West Virginia University Institute of Technology in Beckley, Potomac State College ...

in 1951 and a PhD from

Ohio State University The Ohio State University, commonly called Ohio State or OSU, is a public land-grant research university in Columbus, Ohio. A member of the University System of Ohio, it has been ranked by major institutional rankings among the best publ ...

in 1955, working with

Melville L. Wolfrom Melville Lawrence Wolfrom (April 2, 1900 – June 20, 1969) was an American chemist. Early life, education, and career Melville Wolfrom's grandfather Johann Lorenz Wolfrum immigrated to the United States from Aš in 1854, and was of Sudeten Germ ...

on periodate oxidations.

Research and career

Bobbitt worked from 1952 to 1955 as a teaching assistant at Ohio State. He then moved to

Wayne State University Wayne State University (WSU) is a public research university in Detroit, Michigan. It is Michigan's third-largest university. Founded in 1868, Wayne State consists of 13 schools and colleges offering approximately 350 programs to nearly 25,000 ...

, as a postdoctoral fellow in the research group of

Carl Djerassi Carl Djerassi (October 29, 1923 – January 30, 2015) was an Austrian-born Bulgarian-American pharmaceutical chemist, novelist, playwright and co-founder of Djerassi Resident Artists Program with Diane Middlebrook, Diane Wood Middlebrook. He is b ...

, working on

isoquinoline Isoquinoline is a heterocyclic aromatic organic compound. It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. In a broader sense, the term isoquin ...

alkaloids Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar st ...

. In 1956, he was hired as a lecturer at the

where he became professor of chemistry from 1969 to 1991. He served as Department Head of Chemistry from 1956 to 1972. In 1992 he became professor emeritus but continued to work in the laboratory, with a focus on oxidation chemistry.Nicholas E. Leadbeater, James M. Bobbitt: ''TEMPO-Derived Oxoammonium Salts as Versatile Oxidizing Agents'', Aldrichimica Acta 47 (2014), S. 65−74. In 1959, he received a

National Science Foundation The National Science Foundation (NSF) is an independent agency of the United States government that supports fundamental research and education in all the non-medical fields of science and engineering. Its medical counterpart is the National I ...

fellowship to work with at the University of Zürich in Switzerland on iridoid glycosides. Bobbitt also worked as a visiting lecturer; from 1964 to 1965 at the

University of East Anglia The University of East Anglia (UEA) is a public research university in Norwich, England. Established in 1963 on a campus west of the city centre, the university has four faculties and 26 schools of study. The annual income of the institution f ...

under the direction of

Alan R. Katritzky Alan Roy Katritzky Fellow of the Royal Society, FRS (18 August 1928 – 10 February 2014) was a British-born American chemist, latterly working at the University of Florida. He was a Heterocyclic compound, heterocyclic chemistry pioneer, who pl ...

; in June 1968 with a short DAAD grant at the University of Kiel with Burchard Franck; from 1971 to 1990 in a collaboration with

Tohoku University , or is a Japanese national university located in Sendai, Miyagi in the Tōhoku Region, Japan. It is informally referred to as . Established in 1907, it was the third Imperial University in Japan and among the first three Designated National ...

in Sendai, Japan with Tetsuji Kametani and Tetsuo Osa on catalytic oxidations; and at

La Trobe University La Trobe University is a public research university based in Melbourne, Victoria, Australia. Its main campus is located in the suburb of Bundoora. The university was established in 1964, becoming the third university in the state of Victoria an ...

in Australia from 1980 to 1981 and at the University of Adelaide in 1985. His research focused on alkaloids, preparative electrochemistry, and oxidation chemistry. Additional research interests included the synthesis of nitrogen heterocycles, thin-layer chromatography, electrolytic oxidation and oxoammonium salt oxidation of alcohols with stoichiometric amounts of

Bobbitt's salt Bobbitt's salt is an oxoammonium compound derived from 4-acetamido-2,2,6,6-tetramethylpiperidine. It contains the tetrafluoroborate anion and is named after the American chemist James M. Bobbitt. As a less expensive analogue of the ''N''-oxoam ...

. He developed what became known as the Bobbitt reaction for the synthesis of tetrahydroisoquinoline and its derivatives in 1965.Zerong Wang: ''Comprehensive Organic Name Reactions and Reagents'', John Wiley & Sons, Inc., Hoboken, NJ, p. 441−444, ISBN . In 1968, Bobbitt became lead instructor for an

American Chemical Society The American Chemical Society (ACS) is a scientific society based in the United States that supports scientific inquiry in the field of chemistry. Founded in 1876 at New York University, the ACS currently has more than 155,000 members at all d ...

course on thin-layer chromatography and taught seminars across the US on that subject. In 1970, he became president of the UConn Sigma Xi chapter, and in 1975, the president of the UConn

Phi Beta Kappa The Phi Beta Kappa Society () is the oldest academic honor society in the United States, and the most prestigious, due in part to its long history and academic selectivity. Phi Beta Kappa aims to promote and advocate excellence in the liberal a ...

chapter.

Personal life

Bobbitt met his wife, Jane Ann Hickman, while they were both students at West Virginia University. They had three children: John, Annie, and Laura. In retirement, Bobbitt made wine, raised bees, and gardened, but he remained active in the laboratory and writing papers well into his 80s. Bobbitt was critically injured in a car crash on November 22, 2021, in

Windham, Connecticut Windham is a town in Windham County, Connecticut, United States. It contains the former city of Willimantic as well as the boroughs of Windham Center, North Windham, and South Windham. Willimantic, an incorporated city since 1893, was consoli ...

. He died hours later at

Hartford Hospital Hartford Hospital is an 938-bed acute care teaching hospital located in the South End of Hartford, Connecticut. Hartford Hospital was established in 1854. The hospital campus is located on Seymour Street in Hartford and is directly adjacent to the ...

Books and selected papers

Bobbitt was the author of two books on chromatography and some 120 research articles.

Books

* James M. Bobbitt: ''Thin-layer Chromatography''. Reinhold Publishing Co., New York 1963. * J. M. Bobbitt, A. E Schwarting, and R. J. Gritter, ''Introduction to Chromatography''. Reinhold Publishing, Co. New York (1968), Second Edition, R. J. Gritter, J. M. Bobbitt and A. E. Schwarting, Holden-Day, Inc., Oakland California.

Reviews

* J. M. Bobbitt: Periodate Oxidations of Carbohydrates, ''Advances in Carbohydrate Chemistry'', Vol. 11, 1956, 1-42. * J. M. Bobbitt: The Chemistry of 4-Oxy- and 4-keto-1,2,3,4-tetrahyhdroisoquinolines, ''Advances in Heterocyclic Chemistry'', Vol. 15, 1973, 99-128. (The Bobbitt Reaction). * J. M. Bobbitt, A. J. Bourque: Syntheses of heterocycles using aminoacetals, ''Heterocycles''. Vol. 25, 1987, pp. 601–616. * J. M. Bobbitt and K.-P. Segebarth: The Iridoid Glycosides and Similar Substances, in ''Cyxlopentanoterpine Derivatives'', W. I. Taylor and A. R. Battersby, Eds. Marcel Dekker, 1969, 1-139. * T. Osa, Y. Kashiwagi, J. M. Bobbitt, and Z. Ma: Electroorganic Synthesis on Catalyst Coated Electrodes. In ''Electronic Synthesis'', R. D. Little and N. L. Weinberf, Eds., Marcel Dekker, Inc. New York, 343-354.1991. * J. M. Bobbitt, C. Brückner and N. Merbouh: Oxoammonium Salt and Nitroxide Catalyzed Oxidations of Alcohols. ''Organic Reactions'', Vol. 74, 2009 103-424.

Selected papers

* M. L Wolfrom, J. M. Bobbitt: Periodate oxidation of cyclic 1,3, -diketones. ''Journal of the American Chemical Society'' Vol. 78, 1956, 2489. * C. Djerassi, S. K. Figdor, J. M. Bobbitt, F. I. Markley: Alkaloid studies. XIV. The structure of the cactus alkaloid piloceriene. ''Journal of the American Chemical Society.'' Volume 78, 1956, 3861. * J. M. Bobbitt, H. Schmid, T. B. Africa. Catalpa glycosides. 1. The chararctization of catalposide. ''Journal of Organic Chemistry'' Vol. 26, 1961, 2230. * J. M. Bobbitt, J. C. Sih: Synthesis of isoquinolines. VII. 4-hydroxy-1,2,3,4-tetrahydroisoquinolines. ''Journal of Organic Chemistry''. Vol. 33, 1968, 856-859. * J. M. Bobbitt, A. R. Katritzky, R. D. Kennewell, M. Snarey: Steric requirements of sp2-Hybridized lone electron pairs. Part 1. The conformation of –(pyridylmethylene-onesnes''. J. Chem. Soc (B)'' 1968, 550-553. * J. M. Bobbitt, A. S. Steinfeld, K. H. Weisgraber, S. Dutta: Synthesis of isoquinolines. X. 1-alkyl-1,2,3,4-tetrahydroisoquinoilines. in:''Journal of Organic Chemistry''. Vol. 34, 1969, 2487. * J. M. Bobbitt, I. Noguchi, H. Yagi, K. H. Weisgraber: Electrochemistry of natural Products. III. A stereoselective, stereospecific phenol coupling reaction. In: ''Journal of the American Chemical Society'' 1971, 93, 551. * J. M. Bobbitt, S. J. Huang: A simulated research project in synthetic organic chemistry. An undergraduate laboratory. In:

J. Chem. Educ. The ''Journal of Chemical Education'' is a monthly peer-reviewed academic journal available in both print and electronic versions. It is published by the Division of Chemical Education of the American Chemical Society and was established in 1924 ...

Volume 51, 1974, 58. * J. M. Bobbitt, I. G. C. Coutts, M. R. Hamblin, E.J. Tinley: The enzymatic oxidation of phenolic tetrahydroisoquinoline-1-carboxylic acids. In: ''Journal of the Chemical Society, Perkin Transactions 1'', 1979, pp 2744–2749.

References

External links

* {{DEFAULTSORT:Bobbitt, James M. 1930 births 2021 deaths People from Charleston, West Virginia Ohio State University Graduate School alumni West Virginia University alumni 20th-century American chemists 20th-century American educators University of Connecticut faculty American organic chemists Road incident deaths in Connecticut Chemists from West Virginia