SYNTHETIC APPLICATION OF LITHIATED TRIS(METHYLTHIO)METHANE - PREPARATION OF ALIPHATIC METHYL THIOLCARBOXYLATES FROM THE CORRESPONDING HALIDES - CONVENIENT SYNTHESIS OF TRIS(METHYLTHIO)METHANE

被引：12

作者：

BARBERO, M ^{[1
]}

CADAMURO, S ^{[1
]}

DEGANI, I ^{[1
]}

DUGHERA, S ^{[1
]}

FOCHI, R ^{[1
]}

机构：

[1] UNIV TURIN,IST CHIM ORGAN,VIA P GIURIA 7,I-10125 TURIN,ITALY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 17期

关键词：

D O I：

10.1039/p19930002075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A thorough study directed towards the synthesis of methyl thiolcarboxylates was made on the basis of the following steps: (i) conversion of alkyl halides into the corresponding trimethyl trithioortho-carboxylates by using tris(methylthio) methyllithium in THF at -78-degrees-C; (ii) selective hydrolysis of the intermediates to methyl thiolcarboxylates by using 35% aq. HBF4 in DMSO or, in some cases, in THF. The overall yields of the two stages are, usually, between 70 and 88%. By this procedure it is also possible to incorporate O-18 in the carbonyl group of thiol esters (approximately 98% isotopic purity). Furthermore, a new, convenient method for the preparation of tris(methylthio)methane as the precursor of tris(methylthio)methyllithium was developed.

引用

页码：2075 / 2080

页数：6

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