THERMOLYSIS OF DIAZODICYANOIMIDAZOLE - PRODUCTS AND RATES, THE EFFECT OF 18-CROWN-6

被引：24

作者：

SHEPPARD, WA ^{[1
]}

GOKEL, GW ^{[1
]}

WEBSTER, OW ^{[1
]}

BETTERTON, K ^{[1
]}

TIMBERLAKE, JW ^{[1
]}

机构：

[1] UNIV NEW ORLEANS,DEPT CHEM,NEW ORLEANS,LA 70122

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 10期

关键词：

D O I：

10.1021/jo01324a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intermediate from thermolysis of diazodicyanoimidazole (DDI, 1) is highly electrophilic; for example, it is trapped by aryl halides to form stable aromatic haloylides.3 Structure 2, with the negative charge stabilized by the two cyano groups and the aromatic sextet, has been suggested for this intermediate.3 Form 3 is also a possible structure. If the intermediate is best represented by 2 rather than 3, then nitrogen elimination should be enhanced in polar solvents due to solvation of 2. In addition, since the solid phase stability of DDI is greatly increased in the crystalline 18-crown-6 complex, the solution phase stability of the DDI-18-crown-6 complex is of interest. A similar stabilization has been noted for aryldiazonium salts stabilized as “host-guest” complexes.4-5. © 1979, American Chemical Society. All rights reserved.

引用

页码：1717 / 1719

页数：3

共 12 条

[1] SUBSTITUENT EFFECTS IN RADICAL REACTIONS .3. THERMOLYSIS OF SUBSTITUTED PHENYLAZOMETHANES, 3,5-DIPHENYL-1-PYRAZOLINES, AND AZOPROPANES [J].