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

Marie Kissane; Maureen Murphy; Elisabeth O'Brien; Jay Chopra; Linda Murphy; Stuart G. Collins; Simon E. Lawrence; Anita R. Maguire

doi:10.1039/C0OB00805B

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Organic & Biomolecular Chemistry

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. Lawrence^a and Anita R. Maguire*^b

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

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

Org. Biomol. Chem., 2011,9, 2452-2472

DOI: 10.1039/C0OB00805B
Received 30 Sep 2010, Accepted 17 Dec 2010
First published online 20 Dec 2010

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Abstract
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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.

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Marie Kissane
Maureen Murphy
Elisabeth O'Brien
Jay Chopra
Linda Murphy
Stuart G. Collins
Simon E. Lawrence
Anita R. Maguire

Organic & Biomolecular Chemistry

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

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