Journal or Book Title
The Journal of Organic Chemistry
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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American Chemical Society
Jenks, William S.; Heying, Melanie J.; Stoffregen, Stacey A.; and Rockafellow, Erin M., "Reaction of Dicarbomethoxycarbene with Thiophene Derivatives" (2009). Chemistry Publications. 151.