The Reaction of Tin(IV)-Carbon Bond Towards the Internal Cationic Carbon

Abstract

A series of homologous tin(IV) compounds having leaving groups at the ω-position were synthesized, and their behavior towards Lewis acids was examined.1, 2-Type compounds such as [10] and [14] underwent 1, 2-elimination producing olefins [11] and [13], while 1, 3-type compounds such as [17] underwent 1, 3-elimination producing cyclopropanes [18] With compounds having leaving groups at positions separated by more than three carbons, such as and [37], 1, 5- or 1, 6-hydride shift producing terminal or internal olefins [33], [38] or [39 ]proceeded selectively, provided that the starting materials have hydrogen atom at th e[3 9]appropriate positions. With compounds in which these hydrogens are not available, cyclization to three- or five-membered ring system proceeded. With compounds in which neither the hydride shifts nor cyclization to the ring systems is not possible, the reaction became complicated.