A NEW APPROACH TO REGIOCONTROLLED ENONE TRANSPOSITIONS BASED ON THE FACILE CONVERSION OF α,β-ENONE TOSYLHYDRAZONES TO THE TRANSPOSED ALLYLIC SULFIDES

A new, facile method for the conversion of α,β-enone tosylhydrazones to the transposed allylic sulfides is described which combines sulfenylation of the hydrazone dianions with hydride reduction of the α′-sulfenylated hydrazones. This novel route to allylic sulfides can constitute the sequences for the two directionally different types of enone transposition with 1,2-carbonyl shift.