Synthesis and antifungal testing of 2,4,5,7,9-pentathiadecane 9,9-dioxide has established that the absence of oxygen atoms on S2 significantly attenuates fungitoxicity in accord with our earlier proposal. Attempts to convert that compound into dysoxysulfone led to the discovery of a novel oxidative conversion of unsymmetrical γ-sulfonyl disulfides into the corresponding symmetrical γ-sulfonyl disulfides.
A new cleavage reaction establishes rational access to the title compound. Treatment of the title compound with molecular chlorine establishes that methylsulfonyl is better than chloro as a directing group in the chlorination of unsymmetrical sulfides