Donald C. Kleinfelter, Organic Chemistry

615 Buehler Hall, (865) 974-3392 EMAIL: KLEINFELTER@NOVELL.CHEM.UTK.EDU

        "Rearrangement reactions in the bicyclo[2.2.1] heptane systems have intrigued organic chemists for over 50 years. My students and I have concentrated our more recent efforts on reactions of epoxides in this system. Our studies have included Grignard reactions, hydride reductions, and pinacol-type rearrangements in strongly acidic media.

        We have also studied the products of chromic acid oxidation of certain aryl-substituted tricyclic hydrocarbons, an oxidation presumably involving an epoxide intermediate prior to rearrangement. The cyclic hemiketal final products of the reactions demonstrate interesting physical and chemical properties. One of the former types is restricted rotation of two proximate aryl rings, a process studied by nuclear magnetic resonance. We are pursuing the chemical reactions of these hemiketals as well as studying what effect substituents on the aryl rings have on the barrier to free rotation."

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• Donald C. Kleinfelter, Professor, received his A.B. degree from Gettysburg College and his M.S. and Ph.D. degrees from Princeton University. After spending a year at the University of Delaware and a year at the University of Hawaii, he joined the faculty at UT in 1962. He is the recipient of a UT Alumni Outstanding Teacher Award. Along with C.W. Keenan and J.H. Wood, he has co-authored the last two editions of General College Chemistry, Harper and Row, Publishers.

• D.C. Kleinfelter and G. Sanzero, "Reduction of Some 7-Norbornenols with Lithium Aluminum Hydride-Aluminum Chloride," J. Org. Chem. 1977, 42, 1944.

• D.C. Kleinfelter, T.G. Squires, J.H. Mashburn, R.P. Watsky, and S.B. Brown, "Preparation and Spectral Properties of the 3- p -Tolylsulfenyl- and 3- p -Tolylsulfonyl-2-norbornanols," J. Org. Chem. 1977, 42, 1149.

• T.J. Gerteisen and D.C. Kleinfelter, "The Reactions of Grignard Reagents with Norbornene Oxides," J. Org. Chem. 1971, 36, 3255.

• T.J. Gerteisen, D.C. Kleinfelter, G.C. Brophy, and S. Sternhell, "Properties of 2-Arylnorbornene Oxides and of the Dimer Formed by Dehydration of 2- p - Anisylnorbornane-2,3-Cis-Exo-Diol," Tetrahedron 1971, 27, 3013.

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