Intramolecular iodosilyletherization of alkenylsilanols with bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate

Article abstract of DOI:10.1016/S0040-4039(96)01499-2

Whereas iodonium ion-induced intramolecular cyclization of 3-butenyldiphenylsilanol proceeded via exo mode cyclization to give 5-iodomethyl-2,2-diphenyl-1-oxa-2-silacyclopentane selectively, iodosilyletherization of 4-methyl-3-pentenyldiphenylsilanol afforded 6,6-dimethyl-5-iodo-2,2-diphenyl-1-oxa-2-silacyclohexane exclusively via endo mode cyclization. The oxasilacycloalkanes were converted into the corresponding 1,3-diol and 1,4-diol by oxidative cleavage of the carbon-silicon bond.