73975-55-0Relevant academic research and scientific papers
Transition Metal-Free C-H Thiolation via Sulfonium Salts Using β-Sulfinylesters as the Sulfur Source
Chen, Yanhui,Wen, Si,Tian, Qingyu,Zhang, Yuqing,Cheng, Guolin
supporting information, p. 7905 - 7909 (2021/10/20)
We disclose a direct C(sp)-, C(sp2)-, and C(sp3)-H thiolation reaction using β-sulfinylesters as the versatile sulfur source. The key step of this protocol is chemoselective C-S bond cleavage of the sulfonium salts that are formed in situ from the corresponding alkenes, alkynes, and 1,3-dicarboxyl compounds with β-sulfinylesters. The successful capture of the acrylate byproduct supports a retro-Michael reaction mechanism.
Asymmetric sulfoxidation catalyzed by a vanadium bromoperoxidase: Substrate requirements of the catalyst
Andersson, Malin A.,Allenmark, Stig G.
, p. 15293 - 15304 (2007/10/03)
An investigation of the catalytic effect of vanadium bromoperoxidase (VBrPO, from Corallina officinalis) on the oxidation of a series of prochiral sulfides by hydrogen peroxide, revealed that substrates having a cis- positioned carboxyl group are oxidized
Biotransformation of organic sulfides - VIII. A predictive model for sulfoxidation by Helminthosporium species NRRL 4671
Holland, Herbert L.,Brown, Frances M.,Lakshmaiah, Gingipalli,Larsen, Brett G.,Patel, Manish
, p. 683 - 697 (2007/10/03)
The fungus Helminthosporium species NRRL 4671 converts a wide range of prochiral sulfides to the corresponding chiral sulfoxides, the majority of which have (S) configuration at sulfur. The formation of a series of chiral cyclopentyl alkyl, cyclohexyl alkyl, benzyl alkyl, and methyl alkyl sulfoxides by biotransformation of the corresponding sulfides using Helminthosporium species is described. The analysis of over 90 such biotransformations has resulted in the development of a model based on restrictive-space descriptors that has been used to rationalize these reactions, and that is proposed as a predictor of the outcome of Helminthosporium-catalyzed sulfoxidations.
Enantioselective Liquid Chromatographic Retention of a Series of Sulfoxides and N-Substituted Sulfoximines on Chiral Stationary Phases
Allenmark, Stig,Nielsen, Liselotte,Pirkle, William H.
, p. 325 - 328 (2007/10/02)
With the use of stationary phases comprised of (R)-N-(3,5-dinitrobenzoyl)phenylglycine bound to aminopropyl silica, either covalently via an amide bond (CSP 1) or ionically (CSP 2), the liquid chromatographic behaviour of a series of methoxycarbonyl subst
A New Acid-catalysed Rearrangement of Thiosulphinates to α-Acetylthio-sulphoxides in Acetic Anhydride
Furukawa, Naomichi,Morishita, Tsuyoshi,Akasaka, Takeshi,Oae, Shigeru
, p. 432 - 440 (2007/10/02)
Some thiosulphinates with at least one proton on the carbon adjacent to the sulphenyl sulphur react with acetic anhydride containing acetic acid to afford the corresponding α-acetylthio-sulphoxides.The mechanism of this reaction was studied using thiosulphinates labelled with (2)H, (13)C, and (18)O.These tracer experiments demonstrated that the reaction proceeds via an initial Ei reaction to form the corresponding sulphenic acid ant thioaldehyde followed by recombination in which the sulphur atom of the sulphenic acid adds to the carbon atom of the thioaldehyde, eventually affording the rearranged α-acetylthio-sulphoxide.The formation of the sulphenic acid was confirmed by trapping it with methyl acrylate.The mechanism of the reaction is discussed.
