The Journal of Organic Chemistry

Heteronuclear stabilized carbonium ions. II. N-Aroyl-and aryl-2-oxazolinium cations. Intermediates in a new class of neighboring group reactions

DA Tomalia, JN Paige

Index: Tomalia,D.A.; Paige,J.N. Journal of Organic Chemistry, 1973 , vol. 38, # 3 p. 422 - 430

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Citation Number: 13

Abstract

N-(2-Chloroethyl)-N-acyl/aroyl benzamides/acetamides were solvolyzed under several conditions:(a) in refluxing aqueous acetonitrile;(b) in aqueous acetonitrile with equimolar amounts of AgNOs (25"); and (0) in refluxing methanol. Hydrolyses produced the corresponding amido esters while methanolyses produced equimolar amounts of methyl esters and N-2-chloroethylamides. These solvolyses represent a new class of neighboring ...