Preparation of 3-methylenesilacyclobutane and its use in organic synthesis

Article abstract of DOI:10.1016/0040-4039(95)01710-Y

Treatment of 3-methylene-1,1-diphenylsilacyclobutane (1a) with dihalo-methyllithium provided ring expanded 2-halo-4-methylenesilacyclopentane. Heating a mixture of 1a and carbonyl compound such as PhCHO or PhCOMe at reflux in 1,2-dichloroethane afforded 5-methylene-1,1-diphenyl-2-oxa-1-silacyclohexane which was converted into 3-methylene-1,5-alkanediol monomethyl ether upon treatment with dimethyl acetal in the presence of Lewis acid catalyst. Treatment of ketoaldehyde (PhCOCH₂CH₂CHO) with 1a under BF₃ · OEt₂ catalysis gave 3-methylene-1-phenyl-8-oxabicyclo[3.2.1]octane in one pot.