Iodine-mediated rearrangements of diallylsilanes

Abstract Diallylsilanes can be made to rearrange upon treatment with I 2 . Of the silanes tested, diallyldiphenylsilane showed the greatest propensity to undergo this intramolecular carbocation allylation process. After etherification of the initially formed iodosilane, the products from this transformation represent useful synthetic intermediates, suitable for alkylation and cross-metathesis/annulation reactions.