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

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Date
2011-04-07
Authors
Kissane, Marie
Murphy, Maureen
O'Brien, Elisabeth
Chopra, Jay
Murphy, Linda.
Collins, Stuart G.
Lawrence, Simon E.
Maguire, Anita R.
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RSC Publishing
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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.
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Keywords
2-thio-3-chloroacrylamides , Acetals , E-Z Isomerism , Selenium nucleophiles , Sulfur nucleophiles , Oxygen nucleophiles , Nitrogen nucleophiles , Carbon based nucleophiles
Citation
KISSANE, M., MURPHY, M., O'BRIEN, E., CHOPRA, J., MURPHY, L., COLLINS, S. G., LAWRENCE, S. E. & MAGUIRE, A. R., 2011. Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles. Organic & Biomolecular Chemistry, 9, 2452-2472. doi: 10.1039/C0OB00805B
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©2010, The Authors. Exclusive licence to publish RSC Publishing.