An efficient synthesis of p-quinones utilizing a novel Pummerer-type rearrangement of p-sulfinylphenols
Abstract
Treatment of the p-sulfinylphenol derivatives 1 and 5 with trifluoroacetic anhydride causes a Pummerer-type rearrangement on aromatic rings and concomitant desulfurization to give 1 : 1 mixtures of the corresponding p-quinones and p-dihydroquinones, which are subjected to mild oxidation to provide high yields of p-quinones 3 and 7.