31218-79-8Relevant academic research and scientific papers
One-pot NBS-promoted synthesis of imidazoles and thiazoles from ethylarenes in water
Chen, Liang,Zhu, Huajian,Wang, Jiang,Liu, Hong
, (2019/03/19)
A facile and eco-friendly method has been developed for the synthesis of imidazoles and thiazoles from ethylarenes in water. The reaction proceeds via in situ formation of α-bromoketone using NBS as a bromine source as well as an oxidant, followed by trapping with suitable nucleophiles to provide the corresponding products in good yields under metal-free conditions.
A novel synthesis of aryl methyl sulfones and β-hydroxysulfones from sodium sulfinates and di-tert-butyl peroxide in H2O medium
Lai, Junyi,Yuan, Gaoqing
supporting information, p. 524 - 527 (2018/01/10)
A novel and convenient synthetic route for aryl methyl sulfones and β-hydroxysulfones was developed via the radical reaction between sodium sulfinates and di-tert-butyl peroxide (DTBP). Without any catalysts and additives, the synthetic process could be smoothly carried out to afford the target products in good to excellent yields in H2O medium, demonstrating its promising application. In the present system, H2O could act not only as a green solvent but also as a reactant.
Copper-catalyzed aerobic oxidation and cleavage/formation of C-S bond: A novel synthesis of aryl methyl sulfones from aryl halides and DMSO
Yuan, Gaoqing,Zheng, Junhua,Gao, Xiaofang,Li, Xianwei,Huang, Liangbin,Chen, Huoji,Jiang, Huanfeng
supporting information; experimental part, p. 7513 - 7515 (2012/10/07)
With atmospheric oxygen as the oxidant, a novel copper(i)-catalyzed synthesis of aryl methyl sulfones from aryl halides and widely available DMSO is described. The procedure tolerates aryl halides with various functional groups (such as methoxy, acetyl, chloro, fluoro and nitro groups), which could afford aryl methyl sulfones in moderate to high yields. The copper-catalyzed aerobic oxidation and the cleavage/formation of C-S bond are the key steps for this transformation.
Study of regioselective methanesulfonylation of simple aromatics with methanesulfonic anhydride in the presence of zeolite catalysts
Smith, Keith,Ewart, Gordon M.,El-Hiti, Gamal A.,Randles, Kenneth R.
, p. 3150 - 3154 (2007/10/03)
Regioselective methanesulfonylation of simple aromatics using methanesulfonic anhydride can be achieved over zeolite catalysts. For example, methanesulfonylation of toluene over various cation-exchanged zeolite β catalysts affords higher para-selectivity in the synthesis of methyl tolyl sulfone than standard Friedel Crafts methanesulfonylation utilising aluminium chloride.
Mechanism of oxygenation of aryl methyl and diaryl sulphoxides by peroxomonophosphoric acid
Suthakaran,Rajagopal,Srinivasan
, p. 1369 - 1374 (2007/10/03)
The kinetics of oxygenation of the title sulphoxides by peroxomonophosphoric acid in aqueous acetic acid follows an overall second-order kinetics, first-order in each reactant. An analysis of the influence of [H+] reveals that H3PO5 is the active species in the oxidation. The structure - reactivity studies with different substituents on the phenyl ring give evidence for the formation of an electron deficient sulphonium ion intermediate as the correlation between log k2 and σ gives a negative ρ value (ρ=-0.47±0.09, r=0.988, s=0.03 at 35°C for aryl methyl sulphoxides and ρ=-0.54±0.11, r=0.983, s=0.07 at 35°C for diaryl sulphoxides). It is proposed that the mechanism involves the nucleophilic attack of the sulphoxide sulphur on the peroxo-oxygen of H3PO5 in the rate-limiting step.
Substituent effects in cooxidation: Cr(VI) - oxalic acid - sulfoxides systems
Srinivasan, C.,Jegatheesan, P. Pandarakutty,Rajagopal, S.,Arumugam, N.
, p. 2421 - 2424 (2007/10/02)
The kinetics of cooxidation of several substituted phenyl methyl sulfoxides and oxalic acid with Cr(VI) have been carried out in the presence of perchloric acid.The reaction is first order each in sulfoxide, oxalic acid, Cr(VI), and H1+.The products of oxidation are sulfones and carbon dioxide.Electron-releasing groups in the phenyl ring accelerate the rate while electron-withdrawing groups retard it.The Hammett correlation yields a reaction constant of -0.927 +/- 0.08 (r = 0.994) at 313 K.Addition of aluminum nitrate prevents the occurence of cooxidation.Based on the kinetic information a suitable mechanism has been proposed.Diaryl sulfoxides behave in an analogous manner in the cooxidation.
Mechanism of Oxidation of Aryl Methyl Sulphoxides and Diaryl Sulphoxides by Potassium Bromate
Srinivasan, C.,Jegatheesan, P. Pandarakutty,Arumugam, N.
, p. 678 - 680 (2007/10/02)
The oxidation of aryl methyl and diaryl sulphoxides in aqueous acetic acid at constant and ionic strength is first order each in and .An excellent correlation exists between logk2 and the Hammett ? constants (ρ=-2.05, r=0.997, s=0.05, confidence limit on ρ=+/-0.10 in 50percent aq acetic acid (v/v) at 35 deg for aryl methyl sulphoxides and ρ=-1.82, r=0.992, s=0.12, confidence limit on ρ=+/-0.32 in 75percent aq acetic acid (v/v) at 35 deg for diaryl sulphoxides).The high negative ρ-value in the two series indicates considerable charge development in the transition state.
