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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Date
2010-10-07
Authors
Kissane, Marie
Lynch, Denis
Chopra, Jay
Lawrence, Simon E.
Maguire, Anita R.
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RSC Publishing
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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.
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Diels-Alder , Cycloadditions , Cyclopentadiene , 2,3-dimethyl-1,3-butadiene , 2-thio-3-chloroacrylamides , Cycloadducts , Stereoselectivity
Citation
KISSANE, M., LYNCH, D., CHOPRA, J., LAWRENCE, S. E. & MAGUIRE, A. R. 2010. The influence of reaction conditions on the Diels-Alder cycloadditions of 2-thio-3-chloroacrylamides; investigation of thermal, catalytic and microwave conditions. Organic & Biomolecular Chemistry, 8, 5602-5613. doi: 10.1039/C0OB00368A
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©2010, The Authors. Exclusive licence to publish RSC Publishing.