A New Synthesis of Thiophenes Through Base-Promoted Cyclization of β- and  γ-Alkynyl Thiols

James A. Marshall; William J. DuBay

doi:10.1055/s-1993-22404

Synlett 1993; 1993(3): 209-210
DOI: 10.1055/s-1993-22404

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A New Synthesis of Thiophenes Through Base-Promoted Cyclization of β- and γ-Alkynyl Thiols

James A. Marshall^* , William J. DuBay

^*Department of Chemistry and Biochemistry, The University of South Carolina, Columbia, South Carolina 29208, USA

Abstract

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The β-alkynyl thioacetate 2 and thiocarbonates 7, 8 and 12, obtained from the corresponding alcohols 1, 5, 6 and 11, are readily converted to the thiophenes 4 , 9, 10 and 14, respectively, upon ester cleavage and treatment with KO-t-Bu/ t-BuOH or NaOMe/MeOH. The γ-alkynyl allylic alcohol 15 is likewise converted via the thioacetate 16 and thiol 17 to thiophene 18.

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