Abstract

cf. CA 55, 23400c; Hellmann and Bader, CA 56, 11615h. Treatment of phosphonium salts of the type (Ph3PCH2X)OH(I, X = SMe; II, X = Cl; III, X = Br) with N aq. NaOH gave Ph3PO and MeX. With II and III a Ph group migrated to give Ph2(PhCH2)PO (17% from II, 33% from III). BuLi or PhLi also initiated this rearrangement in nonaq. solvents. The reaction is formulated II + RLi -> Ph3P:CHCl (IV); IV + RLi -> Ph3PRCHCl (V); V -> Ph2PR:CHPh (R = Bu, Ph, or OH). [on SciFinder (R)]

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