Seth Elsheimer
Organic Chemistry

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Associate Professor Ph.D., University of Florida Phone: 407-823-5332 Web page: http://pegasus.cc.ucf.edu/~sethe/ E-mail: sethe@ucf.edu View Full Curriculum Vita

Research
Our research group studies a variety of pure and applied topics. We are particularly interested in-but not limited to-organic molecules that contain fluorine. These fascinating compounds are almost non-existent in nature and therefore the work is based on an entirely synthetic branch of organic chemistry. Several aspects of substituent effects, reaction mechanisms, and synthesis are under investigation. Our most recent research has focused on dietary products fortified with vitamins and minerals.

One of our most significant accomplishments was the demonstration that the mechanism for the alkaline hydrolysis dibromodifluoromethane-alkene adducts-or forms a chemical bond-to a,b-unsaturated carboxylates. Although several mechanisms for the alkaline hydrolysis are conceivable, and such reactions were once believed to occur via a difluorodiene by double dehydrobrominaion, products are still observed from systems in which the diene mechanism is not possible. Although SN2, SN1, SRN1, and monoelimination-addition process appear formally possible, an SN2' mechanism is implicated by studies of model compounds.

Selected Publications

1. "Difluoromethylation of Alkenes via Borohydride Reduction of 1,3-Dibromo-1,1-difluoroalkanes", S. Elsheimer, J. Gonzalez, and C. Foti, J. Org. Chem. 1991, 56, 4323.

2. "3,3-Difluoroallyltrimethylsilane" J. Gonzalez, M.J. Foti, S. Elsheimer, Organic Syntheses 1995, 72, 225.

3. "Halogenation", chapter in book "The Chemistry of Organic Fluorine Compounds II" Edited by M. Hudlicky and A.E. Pavlath. ACS Books, Wash., D.C. 1995.

4. "Reactions of 1,3-Dibromo-1,1-difluoro Compounds with DBU," S. Elsheimer, C. J. Foti, M. D. Bartberger, J. Org. Chem. 1996, 61, 6252.

5. "Mechanisms for the Alkaline Hydrolysis of Dibromodifluoromethane-Alkene Adducts to Alpha,Beta-Unsaturated Carboxylates" S. Elsheimer, J. L. Swanson, J. Gonzalez, J. Fluorine Chem. 2000, 102, 3-9.

6. "Electrochemical Fluorination of Some Industrially Important Organic Compounds" S. N. Misra, A. D. Jethva, M. S. Gohil, S. Elsheimer, G. Ramachandraiah, P.K. Gosh, Reviews in Chemical Engineering 2003, 19(4), 357-385.

Graduate Students
Students working in my laboratory have the to acquire skills in a variety of laboratory and instrumental techniques, coauthor presentations and publications, and develop independence while working on original projects of interest.