Influence of ring size on the outcome of sulfide contraction reactions with thiolactams.: Isolation of bicyclic ketene S,N-acetals and thioisomunchnones

被引：18

作者：

Michael, JP ^{[1
]}

de Koning, CB ^{[1
]}

van der Westhuyzen, CW ^{[1
]}

Fernandes, MA ^{[1
]}

机构：

[1] Univ Witwatersrand, Sch Chem, Inst Mol Sci, ZA-2050 Witwatersrand, South Africa

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 17期

关键词：

D O I：

10.1039/b103560f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction between diethyl bromomalonate and 3-phenylpyrrolidine-2-thione yielded a vinylogous urethane by the Eschenmoser sulfide contraction. However, with 3-substituted piperidine-2-thiones, sulfur was retained in the products, and a range of bicyclic heterocycles. including bicyclic ketene S,N-acetals (2-alkylidene-1,3-thiazolidin-4-ones) and stable thioisomunchnones, was isolated. A novel dimeric ketene SN-acetal was characterised by X-ray crystallography.

引用

页码：2055 / 2062

页数：8

共 8 条

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