83076-99-7Relevant academic research and scientific papers
O-Substituted N-oxy arylsulfinamides and sulfonamides in Michael reactions
Bonifacio, Vasco D. B.,Kumar, Rakesh P.,Prabhakar, Sundaresan,Lobo, Ana M.
experimental part, p. 266 - 276 (2011/11/06)
O-Substituted N-oxy arylsulfinamides and sulfonamides undergo fast aza-Michael reaction in the presence of base and electron-deficient α,β-unsaturated olefins under mild conditions. With N-silyloxy benzenesulfinamides, no aza-Michael product is observed and a hetero aza-Brook type rearrangement takes place induced by the base. Room temperature N-desulfinylation of N-benzyloxybenzenesulfinamide is achieved using BF 3.Et2O. N-Alkoxy arylsulfonamides aza-Michael adducts are found to be generally highly stable under strongly acidic and basic conditions.
Acid-Catalyzed Solvolysis of N-Sulfonyl- and N-Acyl-O-arylhydroxylamines. Phenoxenium Ions
Endo, Yasuyuki,Shudo, Koichi,Okamoto, Toshihiko
, p. 6393 - 6397 (2007/10/02)
The acid-catalyzed reaction of N-acyl- and N-sulfonyl-O-arylhydroxylamines with benzene proceeded quite smoothly to give 2- and 4-hydroxybiphenyls.The results of product analysis, the orientation of the reaction, and the effects of substituents on the nitrogen atom and on the phenyl ring suggested a mechanism that involves a phenoxenium ion.The phenoxenium ion was trapped by benzene and other various nucleophiles.
