α-(METHYLTHIO)BENZYL SULFONES AS SYNTHETIC INTERMEDIATES. PART IV.¹ SOME NEW o-, m- AND p -SUBSTITUTED α-(METHYLTHIO)- AND α,α′-BIS- (METHYLTHIO)-BENZYL SULFONES

Abstract

The reaction of the meta nitro, methoxy and cyano substituted benzylic sulfones with an excess of dimethyl disulfide, in the presence of NaH/DMSO, affords the corresponding α-monosulfenylated derivatives. However, no reaction occurs with the corresponding o-substituted sulfones. A new procedure is developed using S-methyl methanethiosulfonate, in excess, in the “phase transfer condition” which lead for the o-nitro and o-methoxy substituted sulfones to the α-monosulfenylated derivatives and for the o-cyano as well as p- and m-nitro, m-methoxy and m-cyano substituted benzylic sulfones to the corresponding α,α'-bis-sulfenylated derivatives.

Key Words:

• Sulfones
• monosulfenylation
• bis-sulfenylation
• dimethyl disulfide
• S-methyl methanethiosulfonate.