Facile syntheses of allylic allenethiosulfinates and -sulfonates and of beta-iodo and alpha,beta-unsaturated gamma-sultines

The regiospecificity of the 1,4-addition of the reported novel alkoxy chlorodisulfides to 2-methyl-1,3-butadiene is established. Periodate oxidation at room temperature, preferably in the presence of I(sub 2), resulted in oxidative cleavage and cyclization to beta-iodo alpha-beta-unsaturated gama-sultines that were also conveniently prepared by reaction of iodine with alkyl allenesulfinates.