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Reaction of Dicarbomethoxycarbene with Thiophene Derivatives
The Journal of Organic Chemistry
  • William S. Jenks, Iowa State University
  • Melanie J. Heying, Iowa State University
  • Stacey A. Stoffregen, Iowa State University
  • Erin M. Rockafellow, Iowa State University
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Photolysis of derivatives of dimethylmalonate thiophene-S,C-ylide provides dicarbomethoxycarbene, which can react with thiophene to form dimethyl (2-thienyl)malonate. By generation of dicarbomethoxycarbene from the dibenzothiophene-based ylide in neat thiophene, it is shown that the thienylmalonate is not a product of rearrangement of the thiophene ylide, in contrast to thermolysis results. Formation of the thienylmalonate is suppressed by substitution of any sort in the 2- and 5-positions on the thiophene and by substitution with an electron-withdrawing substituent.

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 74(7); 2765-2770. Doi: 10.1021/jo802823s. Copyright 2009 American Chemical Society.

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American Chemical Society
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William S. Jenks, Melanie J. Heying, Stacey A. Stoffregen and Erin M. Rockafellow. "Reaction of Dicarbomethoxycarbene with Thiophene Derivatives" The Journal of Organic Chemistry Vol. 74 Iss. 7 (2009) p. 2765 - 2770
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