Effect of Nucleophilicity and Leaving Group Ability on the SN2 Reactions of Amines with (Acyloxy)alkyl α-Halides: A Product Distribution Study

Article abstract of DOI:10.1021/jo00153a002

The course of the reaction of amines with (acyloxy)alkyl α-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 products 3.The use of a better leaving group also tended to favor the formation of a greater amount of alkylated product.These results have been compared to the observations of Westaway on the effect of leaving group ability and nucleophilicity on the bond lengths in the transit ion state of S_N2 reactions.In addition, secondary amines have been shown to cause the rearrangement of 2-formylbenzamides to 3-amino-1(3H)-isobenzofuranones.