[2,3]-SIGMATROPIC REARRANGEMENT OF YLIDES RESULTING FROM THE REACTIONOF A DIAZOMETHYLPHOSPHONATE WITH ALLYLIC SULFIDES - SYNTHESIS OF NEW ALPHA-PHOSPHORYLATED UNSATURATED SULFIDES

The reaction of diisopropyl diazomethylphosphonate with allylic sulfid es, catalyzed by copper(II) acetylacetonate or rhodium acetate dimer, leads to the corresponding alpha-phosphorylated gamma,delta-unsaturate d sulfides by the [2,3]-sigmatropic Wittig rearrangement of the interm ediate sulfonium ylide. This reaction was successfully extended to alp ha-vinyltetrahydrothiophene and dipropargyl sulfide.