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

Swaroop, T. R. and Roopashree, R. and Ila, H. and Rangappa, K. S. (2013) Attempted Simmon–Smith reaction on b-alkylthio-a,b-unsaturated ketones: A regiospecific synthesis of 2,4-disubstituted thiophenes. Tetrahedron Letters, 54 (2). pp. 147-150. ISSN 0040-4039

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Official URL: http://doi.org/10.1016/j.tetlet.2012.10.110

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 condensation has been suggested.

Item Type: Article
Uncontrolled Keywords: article, 2, unclassified drug, drug synthesis, aldol reaction, thiophene derivative, ketone derivative, sulfur, 4 disubstituted thiophene derivative, beta alkylthio alpha, beta unsaturated ketone derivative, carbene, Simmons Smith reaction
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Arshiya Kousar
Date Deposited: 30 Oct 2019 09:51
Last Modified: 30 Oct 2019 09:53
URI: http://eprints.uni-mysore.ac.in/id/eprint/9666

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