Jump to main content
Jump to site search

Issue 24, 2010
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
01 Jul 2010
Accepted
31 Aug 2010
First published
07 Oct 2010

Org. Biomol. Chem., 2010,8, 5602-5613
Article type
Paper

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

Social activity

Search articles by author

Spotlight

Advertisements