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• 505-23-7 1,3 dithiane 
• 16487-10-8 1,3-dithiane 1-oxide 

Relevant academic research and scientific papers

Ammonium salt catalyzed oxidation of organosulfides to organosulfoxydes

The selective oxidation of aromatic and aliphatic organosulfides with H2O2/H2O catalyzed by metal free ammonium salts has been explored. Reactions were performed using 2.5-5 mol % of catalyst loadings, isolating the corres

Microbiological transformations 36: Preparative scale synthesis of chiral thioacetal and thioketal sulfoxides using whole-cell biotransformations

This work describes the preparative scale enantioselective oxidation of some prochiral dithioacetals and dithioketals to their corresponding chiral monosulfoxides using whole-cell cultures of microorganisms.

Microbiological transformation 35: Enantioselective one-step preparative scale synthesis of 1,3-dithiane-1-oxide via whole-cell bacterial oxidation

This work describes the preparative scale enantioselective oxidation of 1,3-dithiane to the corresponding monosulfoxide using whole-cell cultures of two bacteria, i.e. Acinetobacter calcoaceticus NCIMB 9871 and Pseudomonas sp. NCIMB 9872.

Enantioselective Oxidation of 1,3-Dithioacetals Catalysed by Cyclohexanone Monooxygenase

Cyclohexanone monooxygenase catalysed oxidation of dithioacetals in combination with kinetic resolution gives enantiomerically pure (R)-monosulfoxides.

Donor substituted sulfonyl carbenes, 2: Organothio sulfonyl carbenes

Organothio sulfonyl carbenes 3 have been generated via ylid thermolysis or via α-elimination starting from α-chloro α-organothio sulfones and their derivatives. They have been captured by suitable nucleophilic trapping reagents (diazomethane, enol ethers, and other). Their nucleophilic carbenoid precursors could be trapped by an electrophilic olefin (ketene dithioacetal S,S-dioxides as Michael acceptors). Stable carbene Z-dimers could be obtained under various conditions. Bromine catalyzed isomerization to E-isomers proved to be reversible.

Chemistry of peroxyacyl nitrates. Part III. The oxidation of thioethers by peroxyhexanoyl nitrate

The reaction of peroxyhexanoyl nitrate, 1a, a homologue of the atmospheric pollutant "PAN", 1b, with some twenty thioethers, is described.At 0-25 deg C, common thioethers such as Et2S or PhSMe are rapidly converted into sulfoxides in high yields in a variety of solvents, ranging from pentane and chloroform to acetic acid, methanol and aqueous acetonitrile.Rates are essentially solvent-independent, although the reaction is subject to marked steric hindrance.Relative rates for five p-substituted thioanisoles in MeOH at 22 deg C, leading to a Hammett ρ-value of -1.7, show that the sulfur atoms display nucleophilic character.Electron-attracting groups on α-carbon, such as in PhSCCl3 and in MeSCH2OC(O)Ph, inhibit the formation of sulfoxide.Addition of EtSH lowers the yield of sulfoxide, producing instead EtSSEt and EtSNO.Oxidation of Me2S by 1a with the NO2 group labelled by 18O does not give rise to 18O-enriched DMSO.Comparison of (CH3)2S with (CD3)2S revealed an inverse kinetic H/D isotope effect.The products obtained from 1a vary with solvent.In the presence of water or EtSH, hexanoic acid is formed, while methanol gives rise to methyl hexanoate, and in pentane/hexanoic acid, hexanoic anhydride is produced.In aprotic solvents, significant amounts of CO2 are formed.These observations can best be rationalized on the basis of an intermediate sulfurane R1R2S(ONO2)(OCOR), (I), produced from thioether R1SR2 and 1a, in the first step.The fate of (I) under various conditions is discussed.Finally, the features of the oxidation of thioethers by peroxyacylnitrate are compared with those of acyl peroxides and peroxy esters.It is suggested that in each case formation of a sulfurane may well be the first step.