16487-10-8Relevant articles and documents
Stereoselective Enzyme-catalysed Oxidation-Reduction Reactions of Thioacetals-Thioacetal Sulphoxides by Fungy
Auret, Barbara J.,Boyd, Derek R.,Breen, Fiona,Greene, Ruth M. E.,Robinson, Peter M.
, p. 930 - 933 (1981)
Enzymes present in the fungus Mortierella isabellina catalyse the transfer of an oxygen atom to the cyclic thioacetal 1,3-dithian and from 1,3-dithian 1-oxide, 1,3,5-trithian 1-oxide, and cis-1,3-dithian 1,3-dioxide.The oxidation of 1,3-dithian and the acyclic thioacetal bis-(p-tolylthio)methane to form the corresponding monosulphoxides occurred in the presence of growing cultures of Aspergillus foetidus and a Helminthosporium species.The degree and the preferred direction of stereoselectivity occurring during the asymmetric oxidation and reduction steps was deduced from the enantiomeric excess (e.e.) and absolute stereochemistry of the isolated 1,3-dithian 1-oxide and p-tolylthio-(p-tolylsulphinyl)metane.
[MoO3(2,2″–bipy)]n catalyzed oxidation of amines and sulfides
Tosi, Irene,Vurchio, Carolina,Abrantes, Marta,Gon?alves, Isabel S.,Pillinger, Martyn,Cavani, Fabrizio,Cordero, Franca M.,Brandi, Alberto
, p. 60 - 64 (2018)
The polymeric catalyst [MoO3(2,2′–bipy)]n has been employed in the oxidation of secondary amines to nitrones, and sulfides to sulfoxides or sulfones, using tert–butylhydroperoxide (TBHP) as the stoichiometric oxidant. Whereas the oxi
Reactions between lithiated 1,3-dithiane oxides and trialkylboranes
Saleh, Basil A.,Smith, Keith,Elliott, Mark C.,El-Hiti, Gamal A.
, p. 591 - 603 (2021/09/22)
Various 2-substituted-1,3-dithiane oxides (1-oxide and 1,3-dioxide) have been metalated and reacted for the first time with a trialkylborane (trioctylborane). The 2-chloro-1,3-dioxide results in migration of an octyl group from boron to carbon with the displacement of chloride and gives nonanoic acid after oxidation, but there is no evidence for a second migration involving displacement of a sulfenate group. The reaction involving lithiation of the 2-methoxy-1-oxide results in two migrations, with the displacement of both the methoxy group and the thiolate unit of the dithiane ring, giving dioctyl ketone after oxidation, but the yield is low, primarily because thiophilic addition of the lithiating agent predominates over lithiation. Again, there is no evidence for the displacement of the sulfenate unit. However, the intermediate prior to oxidation can be treated with trifluoroacetic anhydride to induce a Pummerer rearrangement, and the presumed trifluoroacetoxyalkylthiolate group then acts as a novel leaving group and is displaced, resulting in trioctylmethanol on oxidation, but the yield is again very low.
Ammonium salt catalyzed oxidation of organosulfides to organosulfoxydes
Secci, Francesco,Frongia, Angelo,Piras, Pier Paolo
, p. 603 - 605 (2014/01/23)
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