ACETYLENIC ESTERS .3. REACTIONS OF THIOCARBONYL COMPOUNDS WITH METHYL PROPIOLATE METHYL METHYLPROPIOLATE AND METHYL PHENYLPROPIOLATE

被引：21

作者：

DALLAS, G

LOWN, JW

MA, JCN

机构：

[1] Department of Chemistry, University of Alberta, Edmonton, Alta.

来源：

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1968年 / 20期

关键词：

D O I：

10.1039/j39680002510

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Non-terminal acetylenic esters react with many thiocarbonyl compounds to form heterocycles or 1 : 1 addition products. Propiolic esters in most cases form isomeric mixtures of dimethyl 3,3′-thiodiacrylates (I). The stereochemical course of the thiolic nucleophilic additions may be controlled for preparative purposes by changes in solvent polarity. All three stereoisomers of (I) have been prepared. The trans-isomer of methyl 3-(1,1-dimethyl-3-phenyl- 2-isothioureido)acrylate, unlike the cis-, undergoes complete rearrangement to the tetrasubstituted thiourea.

引用

页码：2510 / &