ADDITION OF IODINE-BASED ELECTROPHILIC REAGENTS TO SOME VINYLSILANES

Article abstract of DOI:10.1016/S0040-4020(01)86658-8

The addition of some iodine-based electrophilic reagents to the cyclic vinylsilanes (1) and (4, R=Bu^t, R¹=H) and (4, R=H, R¹=OMe) occurs with high regio- and stereo-specificity to give (2, X=OMe, N3 and NCS) and (5, R=Bu^t, R¹=H, X=OMe and N3) and (5, R=H, R¹=OMe, X=OMe).Similar additions to 2-trimethylsilylhept-1-ene (6) are less efficient and occur with lower regioselectivity.Some of the adducts (2) and (5) have been transformed into functionalised organosilanes.Compounds (10, X=OMe, N3, and NCS) and (12)-(15) are thereby obtained.