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Article
S,C-Sulfonium Ylides from Thiophenes:  Potential Carbene Precursors
The Journal of the American Chemical Society
  • Stacey A. Stoffregen, Iowa State University
  • Melanie Heying, Iowa State University
  • William S. Jenks, Iowa State University
Document Type
Article
Publication Version
Published Version
Publication Date
12-6-2007
DOI
10.1021/ja076351w
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.

Comments

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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Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
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/