Ed W. Warnhoff
Professor Emeritus
A.B., Washington (St. Louis)
Ph. D. , Wisconsin


Organic Chemistry

Current Research Programs:

The research program of an Emeritus professor working on his own is necessarily restricted. An interest in a few of the topics in carbonyl chemistry of long standing interest (see below) can be maintained. There is also the freedom and opportunity to try out new ideas of modest scope unrelated to what has been done in the past. Some specific topics under investigation are:

1.Intramolecular base-catalyzed hydride shifts in ketols; solvent, base, and cation effects on them. What are their geometrical requirements? Can they be used to transfer chirality? How stringent are the restrictions of the Burgi-Dunitz postulate?

2.The Favorskii rearrangement; the interplay of cyclopropanone and semibenzilic mechanisms; cation and nucleophile effects thereon.

3.Hydriodic acid reduction of the aromatic ring.

4.The history of certain aspects of nineteenth century organic chemistry.

Selected Publications:

"When Piperidine Was a Structural Problem." E.W. Warnhoff, Bull. Hist. Chem., 22, 29 (1998)

"The Curiously Intertwined Histories of Benzene and Cyclohexane", E. W. Warnhoff, J. Chem. Educ., 73, 494 (1996).

"Conformational and Steric Effects on Regioselectivity in the Baeyer-Villiger Reaction", V. Dave, J. B. Stothers, and E. W. Warnhoff, Can. J. Chem., 62, 1965 (1984).

"Electronic Effects on Carbon-Chlorine Bonds", E. W. Warnhoff and A. Nakamura, Tetrahedron Lett., 25, 503 (1984).

"Regiospecific Homologation of Unsymmetrical Ketones", V. Dave and E. W. Warnhoff, J. Org. Chem., 48, 2590 (1983).

"Cation-Medium Control of Hydride Transfer Between Carbonyl Groups", E. W. Warnhoff, P. Reynolds-Warnhoff, and M. Y. H. Wong, J. Am. Chem. Soc., 102, 5956 (1980).

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