S,C-Sulfonium Ylides from Thiophenes:  Potential Carbene Precursors

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2007-12-06
Authors
Stoffregen, Stacey
Heying, Melanie
Jenks, William
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Chemistry
Abstract

Photolysis of S,C-sulfonium ylides derived from thioanisol, thiophene, benzothiophene, or dibenzothiophene provides products deriving from dicarbomethoxycarbene. In methanol, no rearrangement of the carbene to the ketene derivative is observed. Formation of dibenzothiophene and benzothiophene is quantitative. For the thiophene-based ylide, insertion of the carbene into the α-CH bond of thiophene is observed. Evidence is presented that supports formation of both singlet and triplet carbene.

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Reprinted (adapted) with permission from The Journal of the American Chemical Society, 129(51); 15746-15747. Doi: 10.1021/ja076351w. Copyright 2007 American Chemical Society.

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Mon Jan 01 00:00:00 UTC 2007
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