Bulletin of the Chemical Society of Japan p. 2965 - 2972 (1982)
Update date:2022-09-26
Topics:
Tanaka, Kazuhiko
Uneme, Hideki
Matsui, Shuichi
Kaji, Aritsune
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 degC 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.
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