85-47-2Relevant articles and documents
Rearrangement of Aromatic Sulfonate Anions in the Gas Phase
Binkley, Roger W.,Flechtner, Thomas W.,Tevesz, Michael J. S.,Winnik, Witold,Zhong, Boyu
, p. 769 - 772 (1993)
Collisionally activated dissociation of deprotonated aromatic sulfonic acids in the gas phase causes rearrangement and fragmentation to produce the corresponding phenoxide ions.The mechanism for this reaction has been investigated and the results of this study favor initial intramolecular nucleophilic addition of a sulfonate oxygen atom to the aromatic ring, a process which is followed by heterolytic cleavage of the carbon-sulfur bond to rearomatize the ring.The product from this addition-elimination sequence is the anion of a sulfurous acid half-ester, which loses SO2 to generate the corresponding phenoxide ion.
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.
Cornforth and Corey-Suggs reagents as efficient catalysts for sulfonation of aromatic and heteroaromatic compounds using NaHSO3 under solvent free and microwave conditions
Fatima, Touheeth,Duguta, Govardhan,Purugula, Venkanna,Yelike, Hemanth Sriram,Kamatala, Chinna Rajanna
, p. 1001 - 1006 (2020/07/27)
Cornforth and Corey-Suggs reagents Pyridinium Dichromate (PDC) and Pyridinium Chlorochromate (PCC) were explored as efficient catalysts for sulfonation of aromatic and heteroaromatic compounds using NaHSO3 in aqueous acetonitrile medium at room temperature within 1–4 h, while microwave assisted reactions took place within 1–4 min under solvent-free conditions. These observations indicate significant rate accelerations in microwave assisted reactions. which were explained due to the bulk activation of molecules induced by insitu generated high temperatures and pressures when microwaves are transmitted through reaction medium.
