Sharply Contrasting Behaviors of phosphonium Salts in Alkaline Decomposition Reactions

Article abstract of DOI:10.1021/jo00230a042

Benzyl<2-(N,N-dimethylamino)phenyl>diphenylphosphonium bromide (3) undergoes alkaline cleavage in 1:1 dioxan-water 1.1*10³ times more rapidly (at 37.7 deg C) than benzyl<4-(N,N-dimethylamino)phenyl>diphenylphosphonium bromide < which gives toluene (100percent) as the hydrocarbon product>.