ChemInform Abstract: Magnesium Amide-Induced Pummerer-Type Reactions of Cyclopropyl Sulfoxides. Synthesis of Cyclopropanone Dithioacetals

The reaction of cyclopropyl phenyl sulfoxide with a magnesium amide, generated from ethylmagnesium bromide and diisopropylamine, gave 1-(phenylthio)cyclopropanol in 72% yield. When the diisopropylmagnesium reagent was treated with a thiol prior to an interaction with cyclopropyl phenyl sulfoxides, symmetrical and unsymmetrical cyclopropanone dithioacetals were produced in fair yields along with small quantities of the corresponding 1-(phenylthio)cyclopropanols.