MECHANISTIC STUDIES IN THE CHEMISTRY OF THIOUREA .2. REACTION WITH BENZIL IN ACID-SOLUTION

被引：16

作者：

BROAN, CJ ^{[1
]}

BUTLER, AR ^{[1
]}

机构：

[1] UNIV ST ANDREWS,DEPT CHEM,ST ANDREWS KY16 9ST,FIFE,SCOTLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1991年 / 10期

关键词：

D O I：

10.1039/p29910001501

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzil reacts with 1,3-dimethylthiourea, 1-methylthiourea, and thiourea in acid solution to give 4,5-diphenyl-4-imidazolines (3) which, in the cases of 1-methylthiourea and thiourea, readily form disulphides 11. Another product of reaction is a bicyclic compound 4 in which it appears that in one thiourea moiety sulphur has been replaced by oxygen. A mechanistic pathway for the formation of 3 and 4 is proposed involving thiourea acting as a sulphur nucleophile, urea as a leaving group, and the thermal decomposition of thiiranes.

引用

页码：1501 / 1504

页数：4