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Issue 31, 2014
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[3+3] Annulation of donor–acceptor cyclopropanes with mercaptoacetaldehyde: application to the synthesis of tetrasubstituted thiophenes

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Abstract

A conceptually new method for synthesis of tetrasubstituted thiophenes in two steps from trans-2-aroyl-3-aryl-cyclopropane-1,1-dicarboxylates and 1,4-dithiane-2,5-diol has been developed. It involves AlCl3-mediated [3+3] annulation of the cyclopropane-derived 1,3-zwitterionic intermediates with in situ generated mercaptoacetaldehyde, followed by DBU-induced rearrangement of the resulting tetrahydrothiopyranols. The target thiophenes are produced in 55–82% yields.

Graphical abstract: [3+3] Annulation of donor–acceptor cyclopropanes with mercaptoacetaldehyde: application to the synthesis of tetrasubstituted thiophenes

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Publication details

The article was received on 22 Jan 2014, accepted on 19 Feb 2014, published on 21 Feb 2014 and first published online on 21 Feb 2014


Article type: Communication
DOI: 10.1039/C4CC00565A
Citation: Chem. Commun., 2014,50, 4062-4064
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    [3+3] Annulation of donor–acceptor cyclopropanes with mercaptoacetaldehyde: application to the synthesis of tetrasubstituted thiophenes

    G. Sathishkannan and K. Srinivasan, Chem. Commun., 2014, 50, 4062
    DOI: 10.1039/C4CC00565A

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