119784-44-0Relevant academic research and scientific papers
Thermal conversion of primary alcohols to disulfides: Via xanthate intermediates: An extension to the Chugaev elimination
He, Wei,Ding, Yong,Tu, Jianzhuo,Que, Chuqiang,Yang, Zhanhui,Xu, Jiaxi
, p. 1659 - 1666 (2018)
Primary alcohols are converted into dialkyl disulfides via heating in situ generated O-alkyl S-difluoro(ethoxycarbonyl)methyl xanthates from ethyl bromodifluoroacetate and potassium xanthates, prepared from primary alcohols and carbon disulfide in the presence of KOH. The reaction mechanism is suggested as an alkyl C[1,3] shift followed by a radical mechanism. This extends to the Chugaev elimination which yields olefins. The current research provides easy access to dialkyl disulfides from commercially available primary alkanols.
Green Aerobic Oxidation of Thiols to Disulfides by Flavin-Iodine Coupled Organocatalysis
Iida, Hiroki,Kozako, Ryo,Oka, Marina
supporting information, p. 1227 - 1230 (2021/06/21)
Coupled catalysis using a riboflavin-derived organocatalyst and molecular iodine successfully promoted the aerobic oxidation of thiols to disulfides under metal-free mild conditions. The activation of molecular oxygen occurred smoothly at room temperature through the transfer of electrons from the iodine catalyst to the biomimetic flavin catalyst, forming the basis for a green oxidative synthesis of disulfides from thiols.
Generation of thiols by biotransformation of cysteine-aldehyde conjugates with baker's yeast
Huynh-Ba, Tuong,Matthey-Doret, Walter,Fay, Laurent B.,Rhlid, Rachid Bel
, p. 3629 - 3635 (2007/10/03)
Baker's yeast was shown to catalyze the transformation of cysteine-furfural conjugate into 2-furfurylthiol. The biotransformation's yield and kinetics were influenced by the reaction parameters such as pH, incubation mode (aerobic and anaerobic), and substrate concentration. 2-Furfurylthiol was obtained in an optimal 37% yield when cysteine-furfural conjugate at a 20 mM concentration was anaerobically incubated with whole cell baker's yeast at pH 8.0 and 30 °C. Similarly to 2-furfurylthiol, 5-methyl-2-furfurylthiol (11%), benzylthiol (8%), 2-thiophenemethanethiol (22%), 3-methyl-2-thiophenemethanethiol (3%), and 2-pyrrolemethanethiol (6%) were obtained from the corresponding cysteine-aldehyde conjugates by incubation with baker's yeast. This work indicates the versatile bioconversion capacity of baker's yeast for the generation of thiols from cysteine-aldehyde conjugates. Thanks to its food-grade character, baker's yeast provides a biochemical tool to produce thiols, which can be used as flavorings in foods and beverages.
Free-Radical Addition of Heteroarenethiols and Heteroarylmethanethiols to Hexyne and Phenylacetylene. Chemical Behavior of the Transient β-Sulfanylvinyl Radicals
Benati, Luisa,Capella, Laura,Montevecchi, Pier Carlo,Spagnolo, Piero
, p. 7941 - 7946 (2007/10/03)
The free-radical reaction of a number of heteroarenethiols (including 2-thiophene-, 2-benzofuran-, and 2-benzothiophenethiol) and heteroarylmethanethiols (including 2-furyl-, 2-thienyl-, and 3-thienylmethanethiol) with hex-1-yne and phenylacetylene has been investigated in benzene solution both at 100 deg C in the presence of AIBN and at room temperature in the presence of BEt3/O2.Under both of these conditions the above thiols generally furnished transient 2-sulfanylvinyl radicals through regioselective addition of corresponding sulfanyl radicals to the terminal alkyne carbon, but 2-benzofuranthiol failed to react with either alkyne in the presence of BEt3/O2 and unexpectedely gave 2-(ethylsulfanyl)benzofuran to a significant extent.The produced 2-(2-heteroarylsulfanyl)vinyl radicals largely preffered to undergo intramolecular H-abstraction reaction rather than intramolecular 5-endo cyclization onto the heteroaryl moiety of the 2-sulfanyl substituent.The 2-- and, especially, 2-vinyl radicals, besides H-abstraction, promptly underwent intramolecular 5-exo cyclization to give spiro radicals that interestingly underwent β-scission of their respective C-S and C-O bond resulting in ring cleavage of the original heteroaryl group.The 2-vinyl radicals did not exhibit any similar 5-exo cyclization, but did undergo a 6-endo cyclization to a very slight extent.
