“…[6][7][8] Oxidation of aromatic disulfides with Pb(OAc) 4 in alcohols resulting in sulfinic esters is most extensively studied. 9 Chlorine dioxide was success fully used in the synthesis of dialkyl and diaryl thiosul fonates, sulfonic acids, and sulfonyl chlorides.…”
Oxidation of diisobornyl disulfide with m chloroperoxybenzoic acid, lead tetracetate, and chlorine dioxide was studied. Depending on the reaction conditions, the following products with the increasing oxidation number of the sulfur atom were obtained: diisobornyl trisulfide, isobornyl isobornanethiosulfinate, isobornanesulfinyl chloride, isobornanesulfinic, isobornane sulfonic acid and their esters.
“…[6][7][8] Oxidation of aromatic disulfides with Pb(OAc) 4 in alcohols resulting in sulfinic esters is most extensively studied. 9 Chlorine dioxide was success fully used in the synthesis of dialkyl and diaryl thiosul fonates, sulfonic acids, and sulfonyl chlorides.…”
Oxidation of diisobornyl disulfide with m chloroperoxybenzoic acid, lead tetracetate, and chlorine dioxide was studied. Depending on the reaction conditions, the following products with the increasing oxidation number of the sulfur atom were obtained: diisobornyl trisulfide, isobornyl isobornanethiosulfinate, isobornanesulfinyl chloride, isobornanesulfinic, isobornane sulfonic acid and their esters.
“…(S)-tert-Butyl tert-butanethiosulfinate 6 was prepared according Ellman 1 . For ee determination: racemic sulfoxides and subsequent racemic products were synthesised starting from racemic tert-butyl tert-butanethiosulfinate prepared according Freeman 2 .…”
Enantiopure aromatic (phenyl, naphthyl) and heteroaromatic (pyridyl, quinolyl, diazinyl) sulfoxides have been synthesized by reaction of (S)-tert-butyl tert-butanethiosulfinate with aryl- or heteroaryllithium derivatives. The ortho-directed metalation of the sulfoxides was performed with lithium bases. Subsequent addition of the lithiated intermediates to N-tosylimines afforded tosylaminoalkyl tert-butylsulfinyl arenes. In most cases a complete asymmetric induction was highlighted in favor of (S,S) isomers. Heating the aminosulfoxides provided an original cyclization to form novel cyclic sulfenamides. A novel enantiopure synthesis of a benzylamine was described. An application of an enantiopure aminosulfoxide as N,S ligand for the asymmetric catalysis of allylic nucleophilic substitution has been successfully tested.
“…The thermal stability of 3 in solution is much larger than that of acyclic vic -disulfoxides, RS(O)S(O)R, 3a-c which could be observed below −40 °C, and a little larger than or comparable to that of bridged bicyclic vic -disulfoxides, 8-substituted 6,7-dithiabicyclo[3.2.1]octane 6,7-dioxides 3d. The dioxide 3 showed no tendency to rearrange to the OS- sulfenyl sulfinate [R−S(O)OS−R] in contrast to the behavior of other vic -disulfoxides. 1a,d,2a, Rearrangement−ring expansion would widen the S(1)−C(1)−S(4) angle increasing the unfavorable steric interaction between the two bulky substituents and the neighboring sulfur atoms S(1) and S(4). …”
mentioning
confidence: 98%
“…vic -Disulfoxides (α-disulfoxides) are one of the important intermediates in the oxidation of oligosulfides and have been drawing considerable attention. − Nevertheless, most of them are still elusive and only a few were detected by NMR spectroscopy and have now discovered that the intermediate, giving 2a , is the corresponding tetrathiolane 2,3-dioxide ( 3 ), a vic -disulfoxide, which can be isolated as crystals at room temperature.…”
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