Carboxy(vinyl)ketene intermediates in the thermolysis of methylthio- and methoxy-substituted Meldrum's acid derivatives

被引：15

作者：

Bibas, H ^{[1
]}

Kappe, CO ^{[1
]}

Wong, MW ^{[1
]}

Wentrup, C ^{[1
]}

机构：

[1] Univ Queensland, Dept Chem, Brisbane, Qld 4072, Australia

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1998年 / 03期

关键词：

D O I：

10.1039/a708585k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methylthio- and methoxy-substituted carboxy(vinyl)ketenes 10 and 16a have been identified by Ar matrix isolation FTIR spectroscopy following flash vacuum thermolysis (FVT) of Meldrum's acid derivatives 7 and 13a, Methylthio(methyl)methyleneketene 9 and alkoxy(methyl)methyleneketene 15 are formed concurrently at high FVT temperatures. The alkoxy(methyl)methyleneketenes 15 do not isomerise to alkoxy(vinyl)ketenes 18, which have been generated and identified in other reactions. Ethoxy(methyl)methyleneketene 15b readily eliminates ethene in a retro-ene type reaction to produce acetylketene 22. Ketenes 15 react with alcohols and amines to produce 3-alkoxybutenoic acid derivatives 21.

引用

页码：493 / 498

页数：6

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