Reaction of Dicarbomethoxycarbene with Thiophene Derivatives

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Date
2009-03-02
Authors
Jenks, William
Heying, Melanie
Jenks, William
Stoffregen, Stacey
Rockafellow, Erin
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Chemistry
Abstract

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.

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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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