55735-62-1

Upstream product

• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 
• 696-63-9 4-Methoxybenzenethiol 
• 6214-19-3 methyl p-methoxybenzenesulfonate 
• 75-04-7 ethylamine 
• 154853-46-0 2,4-dinitrophenyl 4-methoxybenzenesulfonate 
• 459-73-4 GlyOEt*HCl 
• 100-46-9 benzylamine 
• 1213779-62-4 5-N,N-dimethylaminosulfonyl-8-(4-methoxybenzenesulfonyloxy)quinaldine 

Relevant academic research and scientific papers

Reduction of o-iodosobenzoate ion by sulfides and its oxidative regeneration

o-Iodosobenzoate and o-iodoxybenzoate ion (IBA and IBX, respectively) are turnover catalysts of hydrolyses of phosphonofluoridates and non-toxic simulants. Reactions of IBA with phosphonothioates are stoichiometric because sulfides (e.g. 4-methoxybenzenet

Photochemical cleavage reactions of 8-quinolinyl sulfonates in aqueous solution

Photochemical cleavage reactions of 8-quinolinyl benzenesulfonate derivatives and related sulfonates in aqueous solutions are reported. The 8-quinolinyl benzenesulfonates undergo photolysis upon photoirradiation at 300-330 nm to give the corresponding 8-quinolinols and benzenesulfonic acids with the production of only negligible amounts of byproducts. The effects of substituent groups of the 8-quinolinyl moiety and the benzene ring on the photolysis reactions were examined. Based on steady-state mechanistic studies using a triplet sensitizer, a triplet quencher, and electron donors, it was suggested that the photolysis proceeds mainly via the homolytic cleavage of S-O bonds in the excited triplet state.

Regioselectivity and the nature of the reaction mechanism in nucleophilic substitution reactions of 2,4-dinitrophenyl X-substituted benzenesulfonates with primary amines

Second-order rate constants have been measured for the reaction of 2,4-dinitrophenyl X-substituted benzenesulfonates with a series of primary amines. The nucleophilic substitution reaction proceeds through competitive S-O and C-O bond fission pathways. The S-O bond fission occurs dominantly for reactions with highly basic amines or with substrates having a strong electron-withdrawing group in the sulfonyl moiety. On the other hand, the C-O bond fission occurs considerably for the reactions with low basic amines or with substrates having a strong electron-donating group in the sulfonyl moiety, emphasizing that the regioselectivity is governed by both the amine basicity and the electronic effect of the sulfonyl substituent X. The apparent second-order rate constants for the S-O bond fission have resulted in a nonlinear Bronsted-type plot for the reaction of 2,4-dinitrophenyl benzenesulfonate with 10 different primary amines, suggesting that a change in the rate-determining step occurs upon changing the amine basicity. The microscopic rate constants (k1 and k2/k-1 ratio) associated with the S-O bond fission pathway support the proposed mechanism. The second-order rate constants for the S-O bond fission result in good linear Yukawa-Tsuno plots for the aminolyses of 2,4-dinitrophenyl X-substituted benzenesulfonates. However, the second-order rate constants for the C-O bond fission show no correlation with the electronic nature of the sulfonyl substituent X, indicating that the C-O bond fission proceeds through an SNAR mechanism in which the leaving group departure occurs rapidly after the rate-determining step.

The Hammett equation and micellar effects on SN2 reactions of methyl benzenesulfonates - The role of micellar polarity

Substituent effects on the reaction of H2O, OH-, and Br- with p-substituted methyl benzenesulfonates in cationic micelles of cetyl trialkylammonium ion surfactants (n-C16H33NR3X, X = OH, Br, R = Me, Et, nPr, nBu) and in water were analyzed by using the Hammett equation. Values of p in the various media confirm that micellar interfacial regions are less polar than water and polarities decrease with increasing bulk of the surfactant head-group. Wiley-VCH Verlag GmbH, 2000.

Micellar Effects upon Spontaneous and Carboxylate Ion Catalyzed Hydrolyses of Benzenesulfonyl Chlorides

Spontaneous hydrolyses of benzenesulfonyl chlorides are inhibited by micelles of cetyltrimethylammonium chloride (CTACl), sodium dodecyl sulfate (SDS), and N-hexadecyl-N,N-dimethyl-3-ammonio-1-propanesulfonate (SB3-16).The rate constants for hydrolyses of fully bound substrates are similar in CTACl and SB3-16.The rate constants in CTACl (k+) and SDS (k-) depend on the electronic effects of the 4-substituents and k+/k- increases in the sequence MeO Me H Br NO2.These micellar charge effects are ascribed to changes in the extents of bond-making and -breaking in the transition state.Hydrolysis in micellized N-dodecyl-N,N-dimethylglycine (B1-12) is inhibited, but this effect is offset by nucleophilic participation by the carboxylate moiety.Electron-withdrawing substituents strongly favor nucleophilic participation and for the 4-bromo and 4-nitro derivatives second-order rate constants in zwittwerionic betaine micelles of B1-12 are similar to those for reaction with nonmicellized N,N,N-trimethylglycine in water.