Facile β-trimethylstannyl promoted 1,5-hydride shifts in cyclooctyl and cyclodecyl systems
Abstract
Deuterium labelling and 2H NMR mapping demonstrate that cyclooctyl and cyclodecyl mesylates in aqueous EtOH exhibit greatly enhanced or exclusive levels of 1,5-hydride shift, provided a Me3Sn group is β to the migrating hydrogen, and after tin group loss from the formal β-stannyl cation, results in regiospecific, transannular alkene formation.