The Journal of Organic Chemistry

Nucleophilic substitution at centers other than carbon: reaction at the chlorine of N-chloroacetanilides with triethylamine as the nucleophile

GR Underwood, PE Dietze

Index: Underwood, Graham R.; Dietze, Paul E. Journal of Organic Chemistry, 1984 , vol. 49, # 26 p. 5225 - 5229

Full Text: HTML

Citation Number: 14

Abstract

The reaction between triethylamine (TEA) and a series of para-substituted N- chloroacetanilides has been studied in aqueous solution buffered to pHs between 1 and 5. In these reactions, the exclusive product derived from the aromatic moiety is the corresponding acetanilide. The reaction occurs via two parallel pseudo-second-order paths, one acid catalyzed (the Orton-like mechanism), the other uncatalyzed. The uncatalyzed ...