The Journal of Organic Chemistry

Reaction of (acyloxy) alkyl. alpha.-halides with phenols: effect of nucleofugicity and nucleophilicity on product distribution

KB Sloan, SAM Koch

Index: Sloan, Kenneth B.; Koch, Suzanne A. M. Journal of Organic Chemistry, 1983 , vol. 48, # 21 p. 3777 - 3783

Full Text: HTML

Citation Number: 24

Abstract

The product distribution obtained from the reaction of (acy1oxy) alkyl a-halides (1 or 5) with phenols was found to depend on the nucleophilicity of the phenol, the nucleofugicity of the leaving group, and the ability of the electrophile to stabilize a carbenium ion. More nucleophilic phenols tended to give more acylation while better leaving groups and more stable incipient carbenium ions in the electrophile tended to favor the formation of ...