Hydrosilylation of methylenecyclopropane and methylenecyclobutane with dichloro(methyl)silane and synthesis of novel acetylenic silahydrocarbons from the reaction products

Abstract

Hydrosilylation of methylenecyclopropane with dichloro(methyl)silane involves not only addition to the multiple bond, but also results in opening of the three-membered ring to form dichloro(cyclopropylmethyl)methylsilane and 1,4-bis(dichloromethylsilyl)butane. Dichloro(cycloalkylmethyl)methylsilanes were converted into the corresponding (cycloalkylmethyl)(diethynyl)methylsilanes by reaction with ethynylmagnesium bromide. The reaction of bis(bromomagnesioethynyl)(cyclobutylmethyl)methylsilane with dichlorodimethylsilane leads to cyclotetrasilaethyne framed with methyl and cyclobutyl groups. From 1,4-bis-[dichloro(methyl)silyl]butane and bis[(bromomagnesioethynyl)dimethylsilyl]ethyne or -ethene, 22-membered macrobicyclic highly unsaturated silahydrocarbons with an endocyclic tetramethylene bridge were synthesized.