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

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