57897-77-5Relevant articles and documents
Correlation of the rates of Solvolysis of 2,1-benzoxathiol-3-one-1, 1-dioxide (2-sulfobenzoic acid cyclic anhydride)
Kevill, Dennis N.,Ryu, Zoon Ha
, p. 561 - 566 (2015)
Solvolysis of acyclic mixed carboxylic-sulfonic anhydrides in hydroxylic solvents is known to involve displacement at the carbonyl carbon to produce a carboxylic acid (water as the nucleophile) and/or an ester (alcohol as the nucleophile) plus the anion of the sulfonic acid. Parallel solvolyses of the cyclic mixed anhydride 2-sulfobenzoic anhydride (structurally similar to phthalic anhydride but with one carbonyl group replaced by a sulfonyl group) involve expulsion from the carbonyl carbon of a sulfonate anion that remains attached as an orthosubstituent in the benzoic acid and/or benzoate ester produced. This complicates the choice of a solvent-ionising-power scale for use in an extended Grunwald-Winstein equation treatment. The YOTs scale, previously recommended as a good general purpose scale, is chosen and used in conjunction with the NT solvent nucleophilicity scale. An acceptable correlation is obtained, which is improved when the two solvents rich in the highly ionising 1,1,1,3,3,3-hexafluoro-2-propanol are excluded. As the solvent is varied, the sensitivities to the changes induced in the two scales are low, consistent with an early transition state, but their ratio has a value which is typical for a pathway involving addition-elimination, with addition rate-determining. Earlier reports, supporting aspects of the proposed mechanism, are reviewed.
Sustainable access to sulfonic acids from halides and thiourea dioxide with air
Zhang, Hui,Wang, Ming,Jiang, Xuefeng
supporting information, p. 8238 - 8242 (2020/12/29)
A sustainable and mild one-step strategy is explored for the synthesis of aryl and alkyl sulfonic acids using a facile combination of halides and sulfur dioxide surrogates under air. The cheap industrial material thiourea dioxide was employed as an eco-friendly and easy-handling sulfur dioxide surrogate, while air was used as a green oxidant. Both aryl and alkyl sulfonic acids were obtained under transition metal-catalyzed or transition metal-free conditions. Mechanistic studies demonstrated that sulfinate was involved as an intermediate in this transformation. Notably, this protocol has been applied to the late-stage sulfonation of the drugs naproxen, isoxepac and ibuprofen.
Arylphosphonylation and arylazidation of activated alkenes
Kong, Wangqing,Merino, Estibaliz,Nevado, Cristina
supporting information, p. 5078 - 5082 (2014/05/20)
Two radical-mediated processes of activated alkenes, namely arylphosphonylation and arylazidation, are described. The difunctionalization of alkenes by a tandem process that involves radical addition, 1,4-aryl migration, and desulfonylation generates α-ar
