REACTIONS OF BENZYL PHENYL SULFIDE NEAT AND IN DENSE POLAR SOLVENTS

The reactions of benzylphenylsulfide (BPS) neat, in tetralin, in dense water, and in supercritical methanol were studied. A free-radical mechanism described the neat pyrolysis of BPS to the major products toluene, thiophenol, diphenyldisulfide, and diphenylsulfide. An analytical rate expression deduced from this mechanism was consistent with results from both neat pyrolysis and copyrolysis with added thiophenol. Reaction in dense water yielded benzaldehyde, whereas reaction in super critical methanol yielded methylphenylsulfide and benzaldehyde, as additional primary products. Thus reaction in water and methanol was by parallel pyrolysis and solvolysis pathways.