CARBODIIMIDE-SULFOXIDE REACTIONS .7. SYNTHESIS OF STABILIZED SULFONIUM YLIDES

被引：116

作者：

COOK, AF

MOFFATT, JG

机构：

[1] Institute of Molecular Biology, Syntex Research, Palo Alto, California

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1968年 / 90卷 / 03期

关键词：

D O I：

10.1021/ja01005a033

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A wide range of compounds containing reactive methylene groups flanked by carbonyl, ester, nitrile, amide, and phosphonate groups have been treated with dicyclohexylcarbodiimide and dimethyl sulfoxide, or other sulfoxides, in the presence of anhydrous phosphoric acid. The products from these reactions have been isolated in crystalline form and characterized as highly stabilized sulfonium ylides. The nuclear magnetic resonance spectra of certain of these ylides provide striking examples of magnetic nonequivalence of aliphatic methylene groups. Possible mechanisms of the reaction are discussed, and the X-ray crystallographic structure of one ylide is presented. © 1968, American Chemical Society. All rights reserved.

引用

页码：740 / &

共 45 条

[1]

BEHRINGER H, 1965, TETRAHEDRON LETT, P1757

[2]

BRIEGER G, 1965, TETRAHEDRON LETT, P3555

[3] SULFOXIDE-CARBODIIMIDE REACTIONS .4. ACID-CATALYZED REACTIONS OF PHENOLS WITH SULFOXIDES AND CARBODIIMIDES [J].