REACTIONS OF LEAD TETRAACETATE .I. FORMATION OF ACYLAMINES FROM PRIMARY CARBOXAMIDES

被引：18

作者：

ACOTT, B

BECKWITH, AL

HASSANAL.A

机构：

[1] Organic Chemistry Department, University of Adelaide

[2] Chemical Laboratories, University of Sussex, Brighton, Sussex

[3] Chemistry Department, University College, Dar-Es-Salam

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1968年 / 21卷 / 01期

关键词：

D O I：

10.1071/CH9680185

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Pentanamide, when treated with lead tetraacetate in hot benzene, affords a mixture of N-butylacetamide and N, N′-dibutylurea. Examples of similar transformations of a number of primary carboxamides are described. The reaction, which may also be conducted in acetic acid or benzene-acetic acid mixture, is catalysed by pyridine. Cyclohexanecarboxamide, when oxidized by lead tetraacetate in the presence of propionic or benzoic acid, is converted into the appropriate acylcyclohexylamine. The reaction mechanism involves intermediate formation of alkyl isocyanate, possibly via Curtius rearrangement of acylnitrene. © 1968 CSIRO. All rights reserved.

引用

页码：185 / &