A New and Convenient Synthetic Method for Cyclopropyl Phenyl Sulfides

Abstract The reactions of a variety of 1,3-bis(phenylthio)propanes with butyllithium have been shown to produce cyclopropyl phenyl sulfides in good to high yields. A new and convenient in situ preparation of 1-lithiocyclopropyl phenyl sulfide can be readily carried out by treating 1,3-bis(phenylthio)propane with 2 equiv. of butyllithium at 0 °C in THF. The reaction with electrophiles proceeds in good yield. O-Aryl and O-alkyl S-cyclopropyl dithiocarbonates also can be prepared in good yields. 1,2-Bis(phenylthio)ethane was converted to phenyl vinyl sulfide on treatment with butyllithium, while 1,4-bis(phenylthio)butane was recovered unchanged by a similar treatment.