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

Year: 2010

Type: article

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.

Source: Organic & Biomolecular Chemistry

DOI: 10.1039/c0ob00805b

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

Institution: University College Cork

Language: English

Topic: Synthesis and Reactivity of Sulfur-Containing Compounds

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: Irish Research Council for Science, Engineering and Technology, University College Cork

OpenAlex ID: W2013540841

FWCI: 0.158

Cites: 40

Cited by: 20

Related to: 10