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

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. [References: 28]