title: Reaction of dicarbomethoxycarbene with thiophene derivatives.
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.
authors.affiliation: Department of Chemistry, Iowa State University, Ames, Iowa 50011-3111, USA. wsjenks@iastate.edu
authors.forename: William S
authors.initials: WS
authors.lastname: Jenks
authors.forename: Melanie J
authors.initials: MJ
authors.lastname: Heying
authors.forename: Stacey A
authors.initials: SA
authors.lastname: Stoffregen
authors.forename: Erin M
authors.initials: EM
authors.lastname: Rockafellow