Reaction of Dicarbomethoxycarbene with Thiophene DerivativesThe Journal of Organic Chemistry
Publication VersionPublished Version
AbstractPhotolysis 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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Copyright OwnerAmerican Chemical Society
Citation InformationWilliam 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
Available at: http://works.bepress.com/william_jenks/9/