74338-75-3Relevant academic research and scientific papers
Extended Pummerer fragmentation mediated by carbon dioxide and cyanide
Liu, Jian,Kragh, Rasmus R.,Kamounah, Fadhil S.,Lee, Ji-Woong
, (2020/10/30)
Pummerer rearrangement reactions generate sulfur (II) oxidation state from sulfur (IV) starting materials in the presence of activating reagents. We found unprecedented transformation of vinyl sulfoxide; disulfide formation reactions mediated by atmospheric pressure of carbon dioxide in extended Pummerer rearrangement reactions. Only under CO2 atmosphere, we observed moderate to high yields of disulfide starting from sulfur (IV) starting materials. Investigations on the reaction mechanism revealed that the degradation of the starting materials and the products was significant in the absence of CO2. Further evidence for the suggested reaction mechanism was obtained by a cross-over experiment and a radical trapping reagent.
1,1,2,2-Tetrahydroperoxy-1,2-diphenylethane as new oxidant for chemoselective and catalyst free oxidation of sulfides to sulfoxides and sulfones
Khosravi, Kaveh,Naserifar, Shirin,Mahmoudi, Boshra,Khalaji, Kobra
, p. 316 - 321 (2017/02/18)
A catalyst free and chemoselective oxidation of sulfides to sulfoxides or sulfones was developed using 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as a new oxidant. This scope has shown the achievement of various sulfoxides and sulfones which were obtained selectively in high yields at room temperature.
A chemoselective oxidation of sulfides to sulfoxides and sulfones using urea-2,2-dihydroperoxypropane as a novel oxidant
Khosravi, Kaveh,Naserifar, Shirin,Asgari, Atefeh
, p. 749 - 756 (2017/02/05)
Background: Sulfoxides and sulfones have been in the center of attention due to their wide range of promises in various approaches. The functional groups presented in these compounds serve as important building blocks in numerous natural, pharmeceutical and agricultural compounds. These deriatives have been prepared through a multitude of routes which were accompanied by several drawbacks. Therefore, there has been an ever-increasing interest to find a new methodology that leads to the production of these compounds via an environmentally benign path bringing about high yields. Recently, gem-dihydroperoxides have attracted much attention due to their oxidizing power and they have been utilized in several oxidation processes. Methods: We carried out a chemoselective oxidation of sulfides to sulfoxides and sulfones on treatment with urea-2,2-dihydroperoxypropane, a solid oxidant composed of equal amounts of 2,2-dihydroperoxypropane and urea, using THF as the solvent under catalyst-free conditions at room temprature. Results: Sulfides possessing a variety of substitutions namely dialkyl, diaryl, ally l and alkyl-aryl were subjected to the optimized reaction conditions and they could successfully afford different amounts of sulfoxides and sulfones depending on the amount of the oxidant utilized. Based on the results, electron-donating groups accelerated the reaction while electron-withdrawing substituents lowered the reactivity. Conclusion: Urea-2,2-dihydroperoxypropane as a solid oxidant which can be stored for several months without any loss in its activity has proved its capability to oxidize sulfides to sulfoxides and sulfones under catalyst-free and mild conditions. This approach is a cost-effective and environmentally benign methodology via which the products have been synthesized in high yields and short reaction times.
Acid-Catalyzed Oxidative Addition of Thiols to Olefins and Alkynes for a One-Pot Entry to Sulfoxides
Yue, Hui-Lan,Klussmann, Martin
supporting information, p. 2505 - 2509 (2016/10/24)
An oxidative variant of the thiol-ene reaction has been developed, achieving the direct addition of thiols to olefins to form sulfoxides. The reaction uses tert-butyl hydroperoxide as oxidant and methanesulfonic acid as catalyst. The latter is believed to catalyze the oxidation of the intermediate sulfide to the sulfoxide. No special precautions are necessary to exclude oxygen, yet the products are formed without oxidation at the β-position. Styrenes, acrylic acid derivatives, alkynes, and thiophenols gave the highest yields, while aliphatic olefins and thiols were less effective.
Pyrimidine-derived disulfides as potential antimicrobial agents: Synthesis and evaluation in vitro
Bonaccorsi, Paola,Barattucci, Anna,Papalia, Teresa,Criseo, Giuseppe,Faggio, Caterina,Romeo, Orazio
, p. 317 - 355 (2015/04/27)
Antibiotic resistance is a worldwide problem. The synthesis and evaluation of new antimicrobial compounds, without cytotoxicity against human cells, are highly desired. In this paper, the preparation of a class of pyrimidine-derived disulfides is describe
Nickel ferrite nanoparticles-hydrogen peroxide: A green catalyst-oxidant combination in chemoselective oxidation of thiols to disulfides and sulfides to sulfoxides
Kulkarni, Aparna M.,Desai, Uday V.,Pandit, Kapil S.,Kulkarni, Makarand A.,Wadgaonkar, Prakash P.
, p. 36702 - 36707 (2014/12/10)
Nickel ferrite nanoparticles-hydrogen peroxide has been demonstrated for the first time as a green and efficient catalyst-oxidant combination in the chemoselective oxidation of thiols to disulfides and sulfides to sulfoxides. This magnetically separable catalyst was found to be reusable for five consecutive runs without appreciable change in the activity, as well as composition of the catalyst. The mechanism for the oxidation of thiols and sulfides has also been proposed. the Partner Organisations 2014.
VO2F(dmpz)2: A new catalyst for selective oxidation of organic sulfides to sulfoxides with H2O2
Hussain, Sahid,Talukdar, Dhrubajyoti,Chaudhuri, Mihir K.,Bharadwaj, Saitanya K.
, p. 6512 - 6515,4 (2012/12/11)
A newly developed and structurally characterized vanadium complex [VO 2F(dmpz)2] (dmpz = 3, 5 dimethyl pyrazole) is reported as recyclable catalyst for the selective oxidation of organic sulfides with H 2O2 in C
Borax-catalyzed and pH-Controlled selective oxidation of organic sulfides by H2O2: An environmentally clean protocol
Hussain, Sahid,Bharadwaj, Saitanya K.,Pandey, Ravindra,Chaudhuri, Mihir K.
experimental part, p. 3319 - 3322 (2011/03/17)
The selective oxidation of sulfides to sulfoxides and sulfones was achieved in high yields at: room temperature with borax as a recyclable catalyst and H2O2 as the terminal oxidant by varying the pH of the reaction medium. The borax/H2O2 system can chemoselectively oxidize alkyl and aryl sulfides in the presence of oxidation-prone functional, groups such as C=C, -CN, and -OH.
Chemoselective sulfoxidation by H2O2 or HNO3 using a phosphate impregnated titania catalyst
Bharadwaj, Saitanya K.,Sharma, Susanda N.,Hussain, Sahid,Chaudhuri, Mihir K.
experimental part, p. 3767 - 3771 (2009/10/11)
A variety of organosulfur compounds have been selectively oxidized to the corresponding sulfoxides by either H2O2 or HNO3 using a newly developed solid acid catalyst composed of 84.5% of TiO2 and 15.5% of [Ti4H11(PO4)9]·nH2O (n = 1-4). The chemoselective oxidation of sulfides in the presence of vulnerable groups such as -CN, -C{double bond, long}C-, -CHO, or -OH, as well as sulfoxidation of substrates like benzothiazole, glycosyl sulfide, and dibenzothiophenes is some of the important attribute of the protocol. Nitric acid, under the present experimental conditions, brings about relatively better selectivity than hydrogen peroxide.
HbA/H2O2: an efficient biomimetic catalytic system for the oxidation of sulfides to sulfoxides
Kumar, Atul,Akanksha
, p. 7857 - 7860 (2008/03/11)
Human hemoglobin (HbA) catalyzed chemo-selective oxidation of sulfides to sulfoxides has been reported using hydrogen peroxide as an oxidant in a phosphate buffer. This biomimetic catalytic procedure was found to be simple, environmentally friendly, selec
