S, C-sulfonium ylides from thiophenes: Potential carbene precursors

SA Stoffregen, M Heying, WS Jenks

Index: Stoffregen, Stacey A.; Heying, Melanie; Jenks, William S. Journal of the American Chemical Society, 2007 , vol. 129, # 51 p. 15746 - 15747

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Citation Number: 19

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 ...