Tetrahedron Letters

Attempted Simmon–Smith reaction on β-alkylthio-α, β-unsaturated ketones: a regiospecific synthesis of 2, 4-disubstituted thiophenes

TR Swaroop, R Roopashree, H Ila, KS Rangappa

Index: Swaroop, Toreshettahally R.; Roopashree, Rangaswamy; Ila, Hiriyakkanavar; Rangappa, Kanchugarakoppal S. Tetrahedron Letters, 2013 , vol. 54, # 2 p. 147 - 150

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Citation Number: 9

Abstract

A new regiospecific route to 2, 4-disubstituted thiophenes has been developed through Simmon–Smith reaction on β-methylthio-α, β-unsaturated ketones. Extension of the reaction to β-ethyl/benzylthio-α, β-unsaturated ketones also gave the corresponding 2, 4- disubstituted thiophenes in a regiospecific manner. A probable mechanism involving a carbenoid methylene insertion to divalent sulfur followed by intramolecular aldol ...