Three consecutive allylic sigmatropic [S–O, S–S, S–C] rearrangements of 1,8-bis(allylthio)naphthalene monooxides via transannular interaction
Abstract
Oxidation of 1,8-bis(allylthio)naphthalene with m-chloroperbenzoic acid (m CPBA) gave the monooxide which undergoes three consecutive sigmatropic rearrangements to afford 2-allylnaphtho[1,8-cd]-1,2-dithiole; the mechanism has been studied using deuterium tracer experiments.