MECHANISM OF ALCOHOLYSIS OF CARBOXYLIC ACID HALIDES IN PRESENCE OF TRIETHYLAMINE

被引：31

作者：

TRUCE, WE

BAILEY, PS

机构：

[1] Department of Chemistry, Purdue University, Lafayette

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 05期

关键词：

D O I：

10.1021/jo01257a030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alcoholysis of carboxylic acid halides in the presence of triethylamine and a hydrocarbon solvent proceeds by two competing pathways, an elimination-addition process involving a ketene intermediate and a substitution process involving an acyl quaternary ammonium intermediate. Evidence for the ketene intermediate was obtained by performing the reaction in the presence of methanol-d and measuring the proportion of monodeuterated ester (in the absence of polydeuterated ester). The products obtained from the isomeric butenoyl chlorides provide further evidence for the competitive processes and suggest the interconversion of the two intermediates. The effects of the leaving group and of the structure of the acyl halide are also presented. © 1969, American Chemical Society. All rights reserved.

引用

页码：1341 / &

共 16 条

[1] DIACYLATION OF WATER AND OF HYDROGEN SULFIDE WITH ACYL CHLORIDE PYRIDINE COMPOUNDS [J].