Tetrahedron p. 389 - 393 (1981)
Update date:2022-08-04
Topics:
McFarland, John W.
Schut, Dirk
Zwanenburg, Binne
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.
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Doi:10.1039/P19810001577
(1981)Doi:10.1021/ja00359a006
(1983)Doi:10.1021/om0001265
(2000)Doi:10.1002/ardp.19813140506
(1981)Doi:10.1039/c4gc00853g
(2014)Doi:10.1021/jo00335a025
(1981)