Tetrahedron p. 10377 - 10388 (1992)
Update date:2022-09-26
Topics:
Bhat
Thomas
Ila
Junjappa
A new general synthesis of 3- and 3,4-substituted 4a-q, 3,4-annelated 7a-d and condensed tricyclic 9a-e thiophenes has been developed through Simmons-Smith reaction of the respective α-oxoketene dithioacetals. Extension of the reaction of α-cinnamoylketene dithioacetals 10a-e and its higher enyl analogs 13a-d, 15a-c gave the corresponding 3-styryl 11a-e and 3-di- and trienyl 14a-d, 16a-c thiophenes in highly regioselective manner. A probable mechanism involving an unusual intramolecular aldol condensation of sulphonium ylid formed through carbenoid methylene insertion on divalent sulfur has been suggested.
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