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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American Chemical Society
Stacey A. Stoffregen, Melanie Heying and William S. Jenks. "S,C-Sulfonium Ylides from Thiophenes: Potential Carbene Precursors" The Journal of the American Chemical Society
Vol. 129 Iss. 51 (2007) p. 15746 - 15747
Available at: http://works.bepress.com/william_jenks/18/