Synthesis of cyclic ethers and allylic sulfides by rearrangement of phenylsulfanyl substituted 1,n-diols with toluene-p-sulfonic acid and with toluene-p-sulfonyl chloride

Abstract

Rearrangement of a series of 1,n-diols (n = 2 to 12), with a PhS-group adjacent to one OH group, under two sets of conditions gives single compounds in excellent yield drawn for four possible classes of products. The effect of the chain length helps in the understanding of the different cyclisation modes and the mechanism of the rearrangements.