25195-40-8Relevant academic research and scientific papers
An efficient approach for the synthesis of novel methyl sulfones in acetic acid medium and evaluation of antimicrobial activity
Bollikolla, Hari Babu,Dasireddy, Chandra Rao,Kotra, Vijay,Ravi Kumar, Gollapudi,Varala, Ravi
, p. 1386 - 1394 (2020/11/20)
A series of nine methyl sulphones (3a-3i) starting from the aldehydes (1a-1i) were synthesized in two consecutive steps. In the first step, preparation of allyl alcohols (2a-2i) from their corresponding aldehydes by the reaction of sodium borohydride in methanol at room temperature is reported. Finally, methyl sulphones are synthesized by condensing sodium methyl sulfinates with allyl alcohols in the presence of BF3.Et2O in acetic acid medium at room temperature for about 2-3 h. The reaction conditions are simple, yields are high (85%-95%), and the products were obtained with good purity. All the synthesized compounds were characterized by their 1H, 13C NMR, and mass spectral analysis. All the title compounds were screened for antimicrobial activity. Among the compounds tested, the compound 3f has inhibited both Gram positive and Gram negative bacteria effectively and compound 3i has shown potent antifungal activity. These promising components may help to develop more potent drugs in the near future for the treatment of bacterial and fungal infections.
Iron (III) chloride-catalyzed direct sulfonylation of alcohols with sodium arenesulfinates
Reddy, M. Amarnath,Reddy, P. Surendra,Sreedhar
supporting information; experimental part, p. 1861 - 1869 (2010/10/21)
A new protocol for the direct sulfonylation of benzylic, allylic and homoallylic alcohols with sodium arenesulfinates is described by using iron (III) chloride as a catalyst and chlorotrimethylsilane as an additive. This method requires no preactivation o
Copper-catalyzed nitrogen loss of sulfonylhydrazones: A reductive strategy for the synthesis of sulfones from carbonyl compounds
Feng, Xing-Wen,Wang, Jian,Zhang, Ji,Yang, Jing,Wang, Na,Yu, Xiao-Qi
supporting information; experimental part, p. 4408 - 4411 (2010/12/19)
Figure Presented. An efficient method for the synthesis of sulfones via nitrogen loss of sulfonyl hydrazones is described. The reaction was performed in the presence of simple copper salt and base by utilization of sulfonyl hydrazones, which were easily p
Novel model sulfur compounds as mechanistic probes for enzymatic and biomimetic oxidations
Penenory, Alicia B.,Argueello, Juan E.,Puiatti, Marcelo
, p. 114 - 122 (2007/10/03)
To test for the intermediacy of sulfide radical cations in biomimetic and enzymatic oxidations, the sulfides PhSCH3 (1a), PhSCH2Ph (1b), PhSCHPh2 (1c), PhSCPh3 (1d), CH 3SCHPh2 (2), PhSCH2CH=CH2 (3), PhSCH2CH=CHPh (4) and CH3SCH2CH=CHPh (5) were studied, and their results were compared to those obtained for the corresponding chemical electron transfer (CET) and photoinduced electron transfer (PET) oxidations. The radical cations generated from 3-5 by CET in the presence of cerium(IV) ammonium nitrate (CAN) yielded only fragmentation products from the alkyl cations and the thiyl radicals (RS.), whereas 2.+ afforded both fragmentation and mainly α-deprotonation products. Photochemical treatment of the sulfides 1a and 1b with C(NO2) 4 gave only the corresponding sulfoxides, while fragmentation was the main pathway for the photoreactions of 1c, 2 and 5, and for 1d only this latter process was observed. These results support our selection of the sulfides RSCHPh2, RSCH2CH=CHPh (R = Me, Ph) and PhSCPh3 as models for the biomimetic and enzymatic studies. As evidenced by the sulfoxides and sulfones detected as unique products both in protic and in aprotic solvents, it is proposed that the mechanism of the biomimetic sulfoxidations of sulfides 1c and 2-5 by TPPFeIIICI is direct oxygen transfer. Three enzymes - Coprinus cinereus peroxidase (CiP), horseradish peroxidase (HRP) and chloroperoxidase (CPO) - were studied in the oxidation of sulfides 1a, 2, 4 and 5. The use of a racemic alkyl hydroperoxide in the CiP enzymatic oxidation of sulfides 5 and 2 yielded the corresponding sulfoxides (23 and 29%) and the aldehyde or benzophenone (5%), respectively. These results suggest the involvement of an ET process for the CiP-catalysed oxidation. Fragmentation products were observed in the enzymatic oxidation of sulfide 4 with HRP, which confirms the previously proposed ET mechanism. On the other hand, the CPO-enzymatic oxidation of sulfide 5 yielded only the corresponding sulfoxide, as would be expected for a direct oxygen-transfer or oxene mechanism. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Studies of Sulfinyl Radicals. 1. Thermal Decompositions of Benzhydryl p-Tolyl Sulfoxide and Benzhydryl Methyl Sulfoxide
Mizuno, Hajime,Matsuda, Minoru,Iino, Masashi
, p. 520 - 525 (2007/10/02)
The kinetics and mechanism of the thermal decompositions of benzhydryl p-tolyl sulfoxide (BTSO) and benzhydryl methyl sulfoxide (BMSO) were studied.Product analysis, ESR, and CIDNP results showed that both sulfoxides gave p-toluenesulfinyl and methanesulfinyl radicals, respectively, by the scission of carbon-sulfur bonds at 100-130 deg C.The presence of a small amount of a base such as pyridine has been found to suppress the formation of other products than the coupling products (the corresponding thiosulfonates and tetraphenylethane), which may be formed by ionic reactions of BTSO and BMSO.The mechanism of BTSO decomposition is complex, since it is in equilibrium with benzhydryl p-toluenesulfenate (BTSN) at 100-130 deg C.On the other hand, BMSO, showing simple decomposition behavior, indicated that the decomposition rates decreased on the addition of hydroxylic solvents.
