TRANSFER OF ALKOXYCARBONYL FROM ALKYL IMIDAZOLIUM-2-CARBOXYLATES TO BENZYL ALCOHOL, A CYCLOHEXANONE ENAMINE AND DIETHYLAMINE

被引：31

作者：

BAKHTIAR, C ^{[1
]}

SMITH, EH ^{[1
]}

机构：

[1] IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,LONDON SW7 2AY,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 03期

关键词：

D O I：

10.1039/p19940000239

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkylimidazole-2-carboxylates may be alkylated with methyl triflate to give the corresponding N-methylimidazolium salts. These salts react with benzyl alcohol in the presence of 1,4-diazabicyclo[2.2.2]octane, with 1-(pyrrolidin-1-yl)cyclohexene and with diethylamine to,give benzyl alkyl carbonates, an enamino ester and a urethane respectively; in one case a tetrahedral intermediate is observed. The corresponding phenyl ester was consumed without attack by benzyl alcohol at the carbonyl group. A 2-cyanoimidazolium salt underwent similar ill-defined consumption whereas a 2-dimethylaminocarbonyl derivative remained unchanged. 2-Methylsulfonylimidazolium salts suffered attack by benzyl alcohol at the ring C-2.

引用

页码：239 / 243

页数：5

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