This article is cited in 4 papers

Communications

Gallium(iii)-mediated dimerization routes for (5-phenyl-2-thienyl)cyclopropane-1,1-dicarboxylate

D. D. Borisov, R. A. Novikov, Yu. V. Tomilov

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: A selectivity-switched dimerization process for (5-phenyl-2-thienyl)cyclopropane-1,1-dicarboxylate under activation conditions with anhydrous Gaiii salts was developed. Using GaCl3 or Ga(NTf2)3 as catalysts, 3a,4,5a,6,7,8-hexahydro-5H-pentaleno[6a,1-b]thiophene and 5,6-dihydro-4H-cyclo-penta[b]thiophene derivatives can be selectively obtained as a result of ipso-type and [3+2]-annulation type dimerization. The crucial role of a phenyl substituent at position 5 of the thiophene ring and some regularities are discussed.

Keywords: Donor–acceptor cyclopropanes, Gallium salts, (Thiophen-2-yl)cyclopropane dicarboxylate, Ipso-dimerization, Pentaleno[6a,1-b]-thiophenes.

Language: English

DOI: 10.1016/j.mencom.2022.03.005

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