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Issue 24, 2010
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The influence of reaction conditions on the Diels–Alder cycloadditions of 2-thio-3-chloroacrylamides; investigation of thermal, catalytic and microwave conditions

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Abstract

The Diels–Alder cycloadditions of cyclopentadiene and 2,3-dimethyl-1,3-butadiene to a range of 2-thio-3-chloroacrylamides under thermal, catalytic and microwave conditions is described. The influence of reaction conditions on the outcome of the cycloadditions, in particular the stereoselectivity and reaction efficiency, is discussed. While the cycloadditions have been attempted at the sulfide, sulfoxide and sulfone levels of oxidation, use of the sulfoxide derivatives is clearly beneficial for stereoselective construction of Diels–Alder cycloadducts.

Graphical abstract: The influence of reaction conditions on the Diels–Alder cycloadditions of 2-thio-3-chloroacrylamides; investigation of thermal, catalytic and microwave conditions

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Publication details

The article was received on 01 Jul 2010, accepted on 31 Aug 2010 and first published on 07 Oct 2010


Article type: Paper
DOI: 10.1039/C0OB00368A
Citation: Org. Biomol. Chem., 2010,8, 5602-5613
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    The influence of reaction conditions on the Diels–Alder cycloadditions of 2-thio-3-chloroacrylamides; investigation of thermal, catalytic and microwave conditions

    M. Kissane, D. Lynch, J. Chopra, S. E. Lawrence and A. R. Maguire, Org. Biomol. Chem., 2010, 8, 5602
    DOI: 10.1039/C0OB00368A

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