AN APPROACH TO THE REACTION MECHANISM OF GEM-DIHALOCYCLOPROPANES WITH METALS UNDER ULTRASONIC IRRADIATION

The reactive intermediate cyclopropylidene, generated quickly by the reactions of dihalocyclopropanes with lithium or magnesium under ultrasonic irradiation, can be trapped by olefins and the corresponding spriopentane derivatives are obtained, Based on the identification of the intermediate and the products of the reaction, a mechanism is proposed that the radical intermediate should be generated at first via a single electron transfer process, sequentially it gains another electron from the metals to form the carbenoid intermediate which then leads to the main products by insertion, addition or rearrangement. On the other hand, it can also abstract the hydrogen atom from the solvent to form the corresponding monohalide which then converts into the cyclopropane derivatives. Discussions on and verifications for the reaction mechanism are given in this paper.