1999 REU Participants

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Kevin Bechtold

Kevin is a senior at St. Cloud State majoring in Chemistry

Synthesis of Fluorinated Oxadiazolines
Kevin Bechtold
St. Cloud State University

Marc Hillmyer
Department of Chemistry, University of Minnesota

Recently, much attention has been given to substituted _3Ð1,3,4Ðoxadiazolines as convenient sources for various types of carbenes. Of specific interest to the Hillmyer group at the University of Minnesota are fluorinated carbenes, for addition to unsaturated polymers. It is hoped that by controlling the amount of fluorine atoms attached to each repeat unit in the polymer, the solubility, as well as other physical characteristics, can be modified to those desired. In the course of this research, syntheses were developed for the generation of substituted _3 Ð 1,3,4 Ð oxadiazolines in general, and 2Ð(2,2,2Ðtrifluroethoxy)Ð2ÐmethoxyÐ5,5ÐdimethylÐ_3Ð1,3,4Ðoxadiazoline in specific. Syntheses of other fluoroalkoxy substituted _3Ð1,3,4Ðoxadiazolines were also attempted, with widely varying results. Attempted addition of methoxyÐ2,2,2Ðtrifluoroethoxy carbene to polyisoprene in a stainless steel vessel at 110o C, and under high nitrogen pressure, was unsuccessful. It is hoped that modification of this procedure will allow addition of the carbene to the polymer to occur.