13284-96-3Relevant academic research and scientific papers
Micellar Photochemistry. Photooxidations with Intramicellar-Generated Singlet Oxygen
Hovey, Michael C.
, p. 4196 - 4202 (1982)
Pyrex-filtered irradiation of an aerated 5percent aqueous sodium dodecyl sulfate (NaDodSO4) solution of 2.8 mM 10-methylphenothiazine (MPT) and 2.8 mM benzyl sulfide resulted in formation of a 39percent yield of benzyl sulfoxide.The reaction was general f
Diselenides and Allyl Selenides as Glutathione Peroxidase Mimetics. Remarkable Activity of Cyclic Seleninates Produced in Situ by the Oxidation of Allyl ω-Hydroxyalkyl Selenides
Back, Thomas G.,Moussa, Ziad
, p. 13455 - 13460 (2003)
A series of aliphatic diselenides and selenides containing coordinating substituents was tested for glutathione peroxidase (GPx)-like catalytic activity in a model system in which the reduction of tert-butyl hydroperoxide with benzyl thiol to afford dibenzyl disulfide and tert-butyl alcohol was performed under standard conditions and monitored by HPLC. Although the diselenides showed generally poor catalytic activity, allyl selenides proved more effective. In particular, allyl 3-hydroxypropyl selenide (25) rapidly generated 1,2-oxaselenolane Se-oxide (31) in situ by a series of oxidation and [2,3]sigmatropic rearrangement steps. The remarkably active cyclic seleninate 31 proved to be the true catalyst, reacting with the thiol via a postulated mechanism in which the thioseleninate 32 is first produced, followed by further thiolysis to selenenic acid 33 and oxidation-dehydration to regenerate 31. In contrast to catalysis with GPx, formation of the corresponding selenenyl sulfide 34 comprises a competing deactivation pathway in the catalytic cycle of 31, as a separate experiment revealed that authentic 34 was a much less effective catalyst than 31. 1,2-Oxaselenane Se-oxide (37), the six-membered homologue of 31, was formed similarly from allyl 4-hydroxybutyl selenide (26), but proved a less effective catalyst than 31. Compounds 31 and 37 are the first examples of unsubstituted monocyclic seleninate esters.
A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent
Anselmi, Silvia,Liu, Siyu,Kim, Seong-Heun,Barry, Sarah M.,Moody, Thomas S.,Castagnolo, Daniele
, p. 156 - 161 (2021/01/14)
A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.
Sulfoxide synthesis from sulfinate esters under Pummerer-like conditions
Kobayashi, Akihiro,Matsuzawa, Tsubasa,Hosoya, Takamitsu,Yoshida, Suguru
supporting information, p. 5429 - 5432 (2020/06/04)
A facile synthetic method for the preparation of allyl sulfoxides byS-allylation of sulfinate esters proceeds through sulfonium intermediates without [3,3]-sigmatropic rearrangement and further Pummerer-type reactions of the resulting allyl sulfoxides. On the basis of the plausible reaction mechanism involving sulfonium salt intermediates,S-alkynylation andS-arylation were also accomplished.
Zinc Bismuthate Zn(BiO3)2. I. A Useful Oxidizing Agent for the Efficient Oxidation of Organic Compounds
Firouzabadi, Habib,Mohammadpour-Baltork, Iraj
, p. 1131 - 1134 (2007/10/02)
Zinc bismuthate is an easily prepared and a stable compound.It could be used as an oxidant in organic solvents under aprotic or in the presence of a catalytic amount of a protic solvent.Primary and secondary saturated, allylic, and benzylic alcohols are converted to their carbonyl compounds in high yields.Mildness of the reagent is shown by the oxidation of thiols to their disulfides in excellent yields.Thioethers are also oxidized to their corresponding sulfoxides in good yields.
Conversion of sulfides to their corresponding sulfoxides with barium permanganate Ba(MnO4)2 under non-aqueous condition
Firouzabadi,Seddighi
, p. 211 - 214 (2007/10/02)
Oxidation of sulfides to their sulfoxides is performed well with barium permanganate in refluxing acetonitrile.
A General Procedure for the Selective Oxidation of Sulfides to Sulfoxides by Nitric Acid: Tetrabromoaurate(III) Catalyst in a Biphasic System
Gasparrini, Francesco,Giovannoli, Mario,Misiti, Domenico,Natile, Giovanni,Palmieri, Gianni
, p. 1323 - 1328 (2007/10/02)
Tetrabromoaurate(III) is an efficient catalyst for the oxidation of sulfides to sulfoxides by nitric acid in a biphasic system (nitromethane/water).The system is selective and can be applied to the oxidation of any type of dialkyl and alkyl aryl sulfide and also of diaryl sulfides activated by electron-releasing substituents.The nature of the active species has been investigated in relation to the mechanistic aspects.
GOLD(III) CATALYZED OXIDATION OF SULFIDES TO SULFOXIDES BY NITRIC ACID UNDER PHASE-TRANSFER CONDITIONS: A NEW SYNTHESIS OF SULFOXIDES
Gasparrini, F.,Giovannoli, M.,Misiti, D.,Natile, G.,Palmieri, G.
, p. 3181 - 3184 (2007/10/02)
Gold(III) halides catalyze the oxidation of sulfides to sulfoxides in a phase-transfer process.The organic sulfides, dissolved in nitromethane, are treated with (Bu4N(1+)*AuCl4(1-)) in catalytic amount and aqueous nitric acid wich acts as an oxidant.The oxidation of the thio-group is selective and can be carried out also in the presence of other oxidizable groups, such as vinyl, tertiary amino, hydroxy, diol etc, which are left unchanged.Moreover in the case of asymmetric disulfides the reaction is regiospecific leading to the fomation of a single monosulfoxide.
