Effect of nucleophilicity and leaving group ability on the SN2 reactions of amines with (acyloxy) alkyl. alpha.-halides: a product distribution study

KB Sloan, SAM Koch

Index: Sloan, Kenneth B.; Koch, Suzanne A. M. Journal of Organic Chemistry, 1983 , vol. 48, # 5 p. 635 - 640

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Citation Number: 25

Abstract

The course of the reaction of amines with (acy1oxy) alkyl a-halides has been found to depend on the nucleophilicity of the amines and the leaving group ability of the halides. More nucleophilic amines tended to give acylated products 2 from the reaction while less nucleophilic amines gave alkylated produds 3. The use of a better leaving group also tended to favor the formation of a greater amount of alkylated product. These results have ...