Reverse selectivity in m-CPBA oxidation of oligothiophenes to sulfones |
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| Authors: | Pappenfus Ted M Melby Jacob H Hansen Brent B Sumption Devin M Hubers Scott A Janzen Daron E Ewbank Paul C McGee Kari A Burand Michael W Mann Kent R |
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| Affiliation: | Division of Science and Mathematics, University of Minnesota, Morris, Minnesota 56267, USA. pappe001@morris.umn.edu |
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| Abstract: | Oligothiophene sulfones of up to six rings can be conveniently prepared by the direct oxidation of butyl-substituted thiophene oligomers with m-CPBA in dichloromethane. Reverse selectivity of oxidized rings is observed relative to previously reported systems without beta-substitution. The selectivity in the trimer and hexamer is confirmed with single-crystal X-ray structure data. The sulfones possess red-shifted absorptions and increased electron affinities relative to the parent oligomers. |
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