123-09-1Relevant articles and documents
Chemistry of Dioxiranes. 6. Electronic Effects in the Oxidation of Sulfides and Sulfoxides by Dimethyldioxirane
Murray, Robert W.,Jeyaraman, Ramasubbu,Pillay, M. Krishna
, p. 746 - 748 (1987)
Dimethyldioxirane (1) oxidizes a series of aryl methyl sulfides to the corresponding sulfoxides.In a separate series of reactions the sulfoxides were oxidized by 1 to the corresponding sulfones.The relative rates of oxidation in both series were treated with the Hammett ρ? relationship.The oxidations were found to be electrophilic in character with ρ values for the sulfide and sulfoxide oxidations equal to -0.77 and -0.76, respectively.
Alkyl Radical Substitution on Disulfide in the Presence of Cobalt(II) Complexes
Tada, Masaru,Sugano, Kiyohiko,Yoshihara, Takao
, p. 2969 - 2974 (1995)
Photolysis of methyl(L)cobaloxime (L=trans ligand) (1) or methyl(L)-O,O'-bis(difluoroboryl)cobaloxime (2) in the presence of bis(4-chlorophenyl) disulfide gave 4-chlorophenyl methyl sulfide together with 4-chlorophenylthio(L)cobaloxime (5) or 4-chlorophenylthio(L)-O,O'-bis(difluoroboryl)cobaloxime (6).Similar photolysis in the presence of 2,2,6,6-tetramethyl-1-piperidyloxyl (TEMPO) gives 1-methoxy-2,2,6,6-tetramethylpiperidine.The reactivity of the cobaloximes 1 and 2 to the disulfide and TEMPO increases when the cobaloximes have a trans ligand (L) of larger steric requirement and low pka, or when the equatorial ligand is an electronegative O-(difluoroboryl)dimethylglyoxime.Two probable mechanisms are proposed for the reaction.The first is a direct radical substitution on the disulfide with a methyl radical, and the second involves the initial interaction between the disulfide and the (L)cobaloxime radical to afford arylthio(L)cobaloxime (5 or 6) and an arylthio radical. the latter radical reacts with methyl(L)cobaloxime to give aryl methyl sulfide.
Production of Alkyl Aryl Sulfides from Aromatic Disulfides and Alkyl Carboxylates via a Disilathiane–Disulfide Interchange Reaction
Nakajima, Takumi,Takano, Ken,Maeda, Hiromu,Ogiwara, Yohei,Sakai, Norio
supporting information, p. 4103 - 4107 (2021/11/10)
The results of this study show that disilathiane is an effective mediator in the synthesis of alkyl aryl sulfides with disulfides and alkyl carboxylates. Mechanistic studies suggest that disilathiane promotes cleavage of the sulfur–sulfur bond of disulfides to generate thiosilane as a key intermediate. Diselenides were also applicable to this transformation to produce the corresponding selenides.
Iodine-promoted ring-opening methylation of benzothiazoles with dimethyl sulfite
Guo, Ying-Qiong,Chen, Fan,Deng, Chen-Liang,Zhang, Xing-Guo
supporting information, p. 1923 - 1926 (2021/03/02)
A halogen-bond promoted ring-opening methylation of benzothiazoles has been developed using dimethyl sulphite as a methylating reagent in the presence of a base. This approach represents a simple and efficient synthesis ofN-methyl-N-(o-methylthio)phenyl amides, and features direct construction of both N-Me and S-Me bonds in a one-pot reaction through the decomposition of easily prepared benzothiazoles.
