81256-17-9Relevant academic research and scientific papers
Hexafluoroisopropanol (HFIP)-prompted rearrangement of N-phenoxysulfonamides for the direct assembly of ortho-sulfonamide phenols: A combined experimental and computational study
Wang, Yi,Chen, Xiaoli,Lin, Shuang,Gao, Hui,Liu, Fu-Xiaomin,Zhou, Zhi,Yi, Wei
supporting information, (2022/01/08)
ortho-Sulfonamide phenols represent a class of attractive structural motifs in medicinal and synthetic chemistry. Herein an efficient metal-free rearrangement reaction has been developed for the construction of ortho-sulfonamide phenols via HFIP-prompted
1,2,3-Benzoxathiazole 2,2-Dioxides: Synthesis, Mechanism of Hydrolysis, and Reactions with Nucleophiles
Andersen, Kenneth K.,Bray, Diana D.,Chumpradit, Sumalee,Clark, Michael E.,Habgood, Gregory J.,et al.
, p. 6508 - 6516 (2007/10/02)
The rate of base-induced hydrolysis of some five-membered cyclic sulfamates, X-3-(p-tolylsulfonyl)-1,2,3-benzoxathiazole 2,2-dioxides (1a, X = H; 1b, X = 5-Me; 1c, X = 5-t-Bu; 1d, X = 5-Br; 1e, X = 5-Cl; 1f, X = 5-Ac; 1g, X = 5-NO2; 8a, X = 6-NO2) were measured in aqueous acetonitrile.The hydrolyses occurred with cleavage of the endocyclic N-SO2 bond.A Hammett plot using ?m values for 1a-g and ?p for 8a had ρ = +2.20.Activation enthalpies and entropies were measured for 1a and for 3-methyl-1,2,3-benzoxathiazole 2,2-dioxide (10).Volumes of activation weredetermined for 1g and for 8a.The mechanistic profile for hydrolysis resembled that for the saponification of the analogous sultones and cyclic sulfates.These first examples of 1,2,3-benzoxathiazole 2,2-dioxides (1a-g, 8a) were prepared by treating N-(2-hydroxyphenyl)-p-toluenesulfonamides with sulfuryl chloride and triethylamine or by oxidizing the monoxide precursors using m-chloroperbenzoic acid.Treatment of 1a with potassium fluoride gave 1,2,3-benzoxathiazole 2,2-dioxide (9), which was methylated to give 10.Sulfamate 1a was treated with various nucleophilic reagents: phenyllithium, methyllithium, potassium fluoride, methylamine, tert-butylamine, and sodium methoxide.The first three attacked the tosyl sulfur atom and cleaved the exocyclic N-SO2 bond.The amines attacked the endocyclic sulfonyl sulfur atom and cleaved the endocyclic N-SO2 bond.Sodium methoxide attacked both sulfonyl groups.
Endocyclic Nucleophilic Substitution at Tetracoordinate Sulfur(VI)
Andersen, Kenneth K.,Chumpradit, Sumalee,McIntyre, Debra J.
, p. 4667 - 4675 (2007/10/02)
A search for endocyclic nucleophilic substitution at tetracoordinate sulfur(VI), usually sulfonyl sulfur, was carried out through the use of molecules so constructed that any intramolecular substitution process was forced to proceed through four-, five-,
Substitution at Tetracoordinate Sulfur(VI). Rearrangement of 2-Aminoaryl Arenesulfonates to N-(2-Hydroxyaryl)arenesulfonamides
Andersen, Kenneth K.,Gowda, Gopala,Jewell, Linda,McGraw, Phillip,Phillips, Brian T.
, p. 1884 - 1889 (2007/10/02)
A series of eight 2-aminoaryl arenesulfonates upon treatment by strong bases rearranged intramolecularly to their corresponding N-(2-hydroxyaryl)arenesulfonamides as did the related tosylates derived from 2-amino-3-hydroxypyridine, 1-amino-2-naphthol, and
