O,S-Dimethyl Carbonodithioate as a Phosgene Substitute for the Preparation of S-Methyl Alkylcarbamothioates and Dialkylcarbamothioates

被引：8

作者：

Degani, Iacopo ^{[1
]}

Fochi, Rita ^{[1
]}

Magistris, Claudio ^{[1
]}

机构：

[1] Univ Turin, Dipartimento Chim Gen & Chim Organ, I-10125 Turin, Italy

来源：

SYNTHESIS-STUTTGART | 2009年 / 22期

关键词：

O; S-dimethyl carbonodithioate; carbamothioates; carbonylation; isomerization; S; S; S-DIMETHYL DITHIOCARBONATE; S-DIALKYL DITHIOCARBONATES; CARBON-MONOXIDE; ALIPHATIC-AMINES; ALLYLIC THIOLS; SULFUR; REARRANGEMENT; ACID; ALKYL; CARBONYLATION;

D O I：

10.1055/s-0029-1218117

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

O,S-Dimethyl carbonodithioate is proposed as a suitable and safely handled reagent that can be used as a replacement for phosgene in the synthesis of S-methyl alkyl- and dialkylcarbamothioates. The former were obtained by a two-step procedure, which can also be carried out in a one-pot fashion without isolating the intermediates O-methyl alkylcarbamothioates; the overall yields of the pure S-methyl alkylcarbamothioates were 94-98%. Optimal conditions for the synthesis of S-methyl dialkylcarbamothioates involved a one-step procedure in a solvent-free system in the presence of triethyl(methyl)ammonium methyl carbonate as a catalyst; yields of the pure products were 85-98%. A mechanism is proposed for the carbamothioate-formation reaction.

引用

页码：3807 / 3818

页数：12