Reverse selectivity in m-CPBA oxidation of oligothiophenes to sulfones

Ted M. Pappenfus, Jacob H. Melby, Brent B. Hansen, Devin M. Sumption, Scott A. Hubers, Daron E. Janzen, Paul C. Ewbank, Kari A. McGee, Michael W. Burand, Kent R Mann

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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 β-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.

Original languageEnglish (US)
Pages (from-to)3721-3724
Number of pages4
JournalOrganic Letters
Volume9
Issue number19
DOIs
StatePublished - Sep 13 2007

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    Pappenfus, T. M., Melby, J. H., Hansen, B. B., Sumption, D. M., Hubers, S. A., Janzen, D. E., Ewbank, P. C., McGee, K. A., Burand, M. W., & Mann, K. R. (2007). Reverse selectivity in m-CPBA oxidation of oligothiophenes to sulfones. Organic Letters, 9(19), 3721-3724. https://doi.org/10.1021/ol071369x