Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance upgrade on Thursday 4th of May 2017 from 8.00am to 9.00am (BST).

During this time our websites will be offline temporarily. If you have any questions please use the feedback button on this page. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 7, 2011
Previous Article Next Article

Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles

Author affiliations

Abstract

Synthetically versatile conjugate addition of a range of carbon, nitrogen, oxygen, sulfur and selenium nucleophiles to the highly functionalised 2-thio-3-chloroacrylamides is described. The stereochemical and synthetic features of this transformation are discussed in detail. In most instances, the nucleophile replaces the chloro substituent with retention of stereochemistry. With the oxygen nucleophiles, a second addition can occur leading to acetals, while with the nitrogen nucleophiles, E-Z isomerism occurs in the resulting enamine derivatives. The ratio of the E/Z isomers can be rationalised on the basis of the substituent and the level of oxidation.

Graphical abstract: Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 30 Sep 2010, accepted on 17 Dec 2010 and first published on 20 Dec 2010


Article type: Paper
DOI: 10.1039/C0OB00805B
Citation: Org. Biomol. Chem., 2011,9, 2452-2472
  •   Request permissions

    Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles

    M. Kissane, M. Murphy, E. O'Brien, J. Chopra, L. Murphy, S. G. Collins, S. E. Lawrence and A. R. Maguire, Org. Biomol. Chem., 2011, 9, 2452
    DOI: 10.1039/C0OB00805B

Search articles by author