Addition of (Methylthio)methyl p-Tolyl Sulfone to α,β-Unsaturated Carbonyl Compounds

Article abstract of DOI:10.1021/jo00354a020

The lithio derivative of (methylthio)methyl p-tolyl sulfone (1) reacted with various α,β-unsaturated carbonyl compounds to afford <1,4> adducts in good to high yields.The introduced (methylthio)(p-tolylsulfonyl)methyl group was easily converted to a (methylthio)carbonyl group or a formyl group.When the reaction of 1 with methyl acrylate using sodium hydride as a base was performed in DMF at an ambient temperature,2-(methoxycarbonyl)-4-(methylthio)-4-(p-tolylsulfonyl)cyclohexanone (8) was obtained in 81 percent yield.Furthermore, 8 was shown to be an important intermediate for preparing 2-substituted 2-(methoxycarbonyl)-1,4-cyclohexanediones.