The Chemistry of Silylcyclopropanes

AbstractThe synthesis and reactions of silylcyclopropanes are reviewed. From the preparative viewpoint, these strained systems can be obtained by the addition of silyl‐substituted carbenes to olefins and of carbenes or carbenoids to vinylsilanes, by condensation of cyclopropyllithiums with chlorosilanes, by ring opening of silyl‐substituted bicyclobutanes and by trimethylsilylmethylenesulfurane addition to α,β‐unsaturated ketones. The susceptibility of this class of molecules to acid‐ and base‐promoted ring openings, electrophilic substitution and thermal rearrangement is detailed. These latter topics and a summary of the use of silylcyclopropanes as cyclopropene precursors are presented in a manner which stresses the unique synthetic utility conveyed by the presence of the silicon atom.