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Issue 7, 2011
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Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles

Marie Kissane,a  Maureen Murphy,a  Elisabeth O'Brien,a  Jay Chopra,a  Linda Murphy,a  Stuart G. Collins,a  Simon E. Lawrencea  and  Anita R. Maguire*b 
Author affiliations

* Corresponding authors

a Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Ireland

b Department of Chemistry and School of Pharmacy, Analytical and Biological Chemistry Research Facility, University College Cork, Ireland
E-mail: a.maguire@ucc.ie

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

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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
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    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

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