Elimination–addition. Part XIV. Addition of carboxylate ions to allenes and acetylenes and use of the adducts in acylation

GD Appleyard, CJM Stirling

Index: Appleyard,G.D.; Stirling,C.J.M. Journal of the Chemical Society [Section] C: Organic, 1967 , p. 2686 - 2691

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Citation Number: 3

Abstract

Base-catalysed additions of acetic, benzoic, and hippuric acids to propadienyl, prop-1-ynyl, and prop-2-ynyl p-tolyl sulphones and to ethynyl phenyl ketone occur readily under mild conditions. The products are 1-(aryl-sulphonylmethyl) vinyl or β-benzoylvinyl esters of the acids and as such are very reactive towards nucleophiles in acylation reactions. Reactions of amines with the sulphonyl esters yield amides. Reactions of the keto-esters, however, ...

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