78388-20-2Relevant academic research and scientific papers
REACTIONS OF N-SULFINYL-p-TOLUENESULFONAMIDE WITH ALCOHOLS
McFarland, John W.,Schut, Dirk,Zwanenburg, Binne
, p. 389 - 393 (1981)
N-Sulfinyl-p-toluenesulfonamide (1) reacted with triaryl- and diarylmethanols to give predominantly N-substituted sulfonamides and SO2 presumably via carbonium ion intermediates.When carbonium ion forming alcohols, such as t-BuOH and Ph2C(Me)OH, were used, the predominant products were alkenes and p-toluenesulfonamide.Allylic alcohols afforded N-substituted sulfonamides, along with dienes and p-toluenesulfonamide.Alcohols wich could not predictably give relatively stable intermediate carbonium ions, gave either dialkyl sulfites or dialkyl ethers, 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 reaction is proposed.
