DIMERIZATION OF CUBENE - 1-IODOADAMANTANE AS A PROBE FOR RADICAL INTERMEDIATES

被引：34

作者：

LUKIN, K ^{[1
]}

EATON, PE ^{[1
]}

机构：

[1] UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 29期

关键词：

D O I：

10.1021/ja00134a009

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fluoride ion induced elimination from 1-bromo- and 1-iodo-2-(trimethyisilyl)cubanes is shown to produce cubene (1) in excellent yield and at high enough concentration for its dimerization to propellane 16. This highly strained compound is unstable; the ultimate reaction pro ducts are characterized as the isomeric bis(tricyclo[4.2.0.0(2,5)]-octa-3,7-diene-3,8-diyl)s 11a,b. These are believed to form via a set of radical ring openings of 16. 1-Iodoadamantane is introduced as an iodine atom donor useful for probing the intermediacy of radicals in the chemistry of highly reactive, strained ring systems such as 16.

引用

页码：7652 / 7656

页数：5

共 28 条

[1] NEW AND IMPROVED METHODS FOR THE RADICAL DECARBOXYLATION OF ACIDS [J].