Reactions of n-sulfinyl-p-toluenesulfonamide with alcohols

N-Sulfinyl p-toluenesulfonamide (1) reacted with triaryl- and diarylmethanols to give predominantly N- substiuted sulfonamides and SO₂ presumably via carbonium ion intermediates. When carbonium ion forming alchols, such as t-BuOH and Ph₂C(Me)OH, were used the predominant products were alkenes and p- toluenesulfonamide. Allytic alcohols afforded N- substiuted sulfonamides along with dienes andp-toluenesulfonamide. Alcohols which could not predictably give relatively stable intermediate carbonium ions, gave either dialkyl sulfites or dialkyl eithers, along with p-toluenesulfonamide. In one case, namely with 9-phenylfluorenol the 1:1 adduct with 1 (an amidosulfite) was isolated. A mechanism for the reactions is proposed.