CHEMISTRY OF YLIDES .19. BETA-CARBONYL SULFONIUM YLIDES

被引：129

作者：

JOHNSON, AW

AMEL, RT

机构：

[1] Chemistry Department, University of North Dakota, Grand Forks, North Dakota

[2] Division of Natural Sciences, University of Saskatchewan, Begina

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 05期

关键词：

D O I：

10.1021/jo01257a012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation, isolation, and physical and chemical properties of dimethylphenacylidenesulfurane (II) and dimethyl(carbomethoxymethylene)sulfurane (la) are described. Both ylides exhibit decreased nucleophilicity and basicity as a result of the derealization of the carbanion electrons through the carbonyl groups, the decrease being larger for II. Spectroscopic methods and chemical reactions (alkylation, acylation, and reaction with carbonyl compounds and nitrosobenzene) served to illustrate the differences. The mechanism of the thermal decomposition of sulfonium ylides to cyclopropanes appears to involve a carbenic moiety. © 1969, American Chemical Society. All rights reserved.

引用

页码：1240 / &

共 44 条

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