Reverse selectivity in m-CPBA oxidation of oligothiophenes to Sulfones

被引：21

作者：

Pappenfus, Ted M. ^{[1
]}

Melby, Jacob H.

Hansenj, Brent B.

Sumption, Devin M.

Hubers, Scott A.

Janzen, Daron E.

Ewbank, Paul C.

Mcgee, Kari A.

Burand, Michael W.

Mann, Kent R.

机构：

[1] Univ Minnesota, Div Sci & Math, Morris, MN 56267 USA

[2] St Catherines Coll, Dept Chem, St Paul, MN 55105 USA

[3] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 19期

关键词：

D O I：

10.1021/ol071369x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3721 / 3724

页数：4

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