The chemistry of stable carbenes .2. Benzoin-type condensations of formaldehyde catalyzed by stable carbenes

被引：1

作者：

Teles, JH ^{[1
]}

Melder, JP ^{[1
]}

Ebel, K ^{[1
]}

Schneider, R ^{[1
]}

Gehrer, E ^{[1
]}

Harder, W ^{[1
]}

Brode, S ^{[1
]}

Enders, D ^{[1
]}

Breuer, K ^{[1
]}

Raabe, G ^{[1
]}

机构：

[1] RHEIN WESTFAL TH AACHEN,INST ORGAN CHEM,D-52074 AACHEN,GERMANY

来源：

HELVETICA CHIMICA ACTA | 1996年 / 79卷 / 01期

关键词：

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Stable carbenes derived from thiazole, 1H-imidazole, and 4H-1,2,4-triazole are efficient catalysts for benzoin-type condensations of formaldehyde. Catalysts derived from N-substituted thiazolium salts trimerize formaldehyde to dihydroxyacetone (II). Catalysts based on 1,4-disubstituted 4H-1,2,4-triazol-1-ium salts give glycolaldehyde (I) as the main product and no II, whereas N,N'-disubstituted 1H-imidazol-3-ium salts yield mixtures of both products. The isolation of several intermediates in the catalytic cycle provide a better insight into the reaction mechanism.

引用

页码：61 / 83

页数：23

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