55854-42-7Relevant academic research and scientific papers
Palladium-catalyzed arylation of aryl sulfonamides with cyclohexanones
Cao, Xiangxiang,Bai, Yang,Xie, Yanjun,Deng, Guo-Jun
, p. 94 - 100 (2014/01/06)
Pd-catalyzed intermolecular aerobic dehydrogenative aromatizations have been developed for the arylation of aryl sulfonamides with cyclohexanones. Various N-aryl sulfonamides were selectively obtained in good yields using molecular oxygen as oxidant. The reaction tolerated a wide range of functionalities.
STUDIES IN THE HETEROCYCLIC COMPOUNDS V. SOME REACTIONS OF 5-CHLORO-2-THIOPHENESULFONYL DERIVATIVES
Obafemi, Craig A.
, p. 119 - 132 (2007/10/02)
The reactions of 5-chloro-2-thiophenesulfonyl chloride are described.Treatment of the sulfonyl chloride with ammonia, hydrazine hydrate, sodium azide, indole and imidazole gave the sulfonamides (5), sulfonohydrazide (4), sulfonyl azide (3), 1-(5-chloro-2-thiophenesulfonyl)indole (27) and 1-(5-chloro-2-thiophenesulfonyl)-imidazole (26), respectively.The sulfonyl chloride was reacted further with 20 aryl and cycloalkyl-amines to give the corresponding sulfonamides (6)-(25).Attempted chlorination of the sulfonyl chloride (2) with sulfuryl chloride or bromination of the sulfonyl azide (3) with pyridinium bromide perbromide failed.However, nitration of the sulfonyl chloride (2) with fuming nitric acid gave the 4-nitro-sulfonyl chloride (28), which with sodium azide afforded the 5-chloro-4-nitro-sulfonyl azide (29).The sulfonyl azides, (3) and (29), have been reacted with triphenylphosphine, triethylphosphite, norbornene and cyclohexene.The azides reacted further with indole and 1-methylindole to give the 2-sulfonyliminoindoles (34)-(36).The infrared spectra and mass spectra of some of the substituted thiophenesulfonyl derivatives are discussed.
Nucleophilic Substitution at Sulphonyl Sulphur.Part 1. Reactivity of Tiophen-2-sulphonyl Halides in Water and Methanol-Acetonitrile
Arcoria, Antonio,Ballistreri, Francesco P.,Musumarra, Giuseppe,Tomaselli, Gaetano A.
, p. 221 - 227 (2007/10/02)
The reactions kinetics of substitued tiophen-2-sulphonyl chlorides and fluorides (5-OMe, 5-Me, H, 5-Cl, 4-NO2, 5-NO2) with anionic and neutral nucleophiles were studied in water at 25 deg C.For the reactions of chlorides with H2O,AcO-,and N3- and for the hydrolysis of fluorides U shaped Hammett plots were observed.For the reaction of sulphonyl chlorides with aniline,pyridine,imidazole,and OH- an approximately linear Hammett correlation is found.Common chloride ion effects on the hyrolysis rate constants appear to be absent.Nucleophilic substitution reactions of substitued thiophen-2-sulphonyl chlorides were also studied in MeOH-MeCN,where the Hammett equation is obeyed.The data appear consistent with an SN2-type mechanism wich can shift toward an SN1 or an SAN process depending on the nucleophile, on the ring substituent, and on the leaving group ability.The application of the More O'Ferrall and Thornton approaches for the prediction of substituent effects on the transition state structure seems to support the above interpretation.
