3379-36-0Relevant articles and documents
Insertion of Benzyne and Substituted Benzynes into the S-S Bond of Diphenyl and Di-p-tolyl Disulfides Yielding the Corresponding o-Bis(arylthio)benzenes
Nakayama, Juzo,Tajiri, Takayuki,Hoshino, Masamatsu
, p. 2907 - 2908 (1986)
Benzyne and substituted benzynes undergo insertion into the S-S bond of diphenyl and di-p-tolyl disulfides to afford the corresponding o-bis(arylthio)benzenes in low but reproducible yields.
Transformations of diphenyl sulfide and diphenylamine on aluminum chloride
Nekhoroshev,Gubaidullin,Yarkova,Nekhorosheva,Nifant’ev,Voronkov,Poleshchuk, O. Kh.,Tarasova
, p. 272 - 277 (2017)
Thianthrene has been synthesized by reacting diphenyl sulfide with AlCl3 in heptane at 98°C for 8 h at a diphenyl sulfide: AlCl3 molar ratio of 2: 1; the thianthrene yield is 58%. The reaction mechanism proposed previously has been confirmed by quantum-chemical calculations; the reaction is characterized by a low negative value of Gibbs free energy, a low heat of reaction, and a high activation energy of the first step. Diphenyl ether and diphenylamine do not enter the test reaction because of low nucleophilicity of the heteroatoms; diphenylamine dimerizes under the reaction conditions to form N,N′-diphenylbenzidine.
Generation of Aryl Radicals from Aryl Halides: Rongalite-Promoted Transition-Metal-Free Arylation
Yu, Fazhi,Mao, Runyu,Yu, Mingcheng,Gu, Xianfeng,Wang, Yonghui
, p. 9946 - 9956 (2019/09/04)
A new and practical method for the generation of aryl radicals from aryl halides is reported. Rongalite as a novel precursor of super electron donors was used to initiate a series of electron-catalyzed reactions under mild conditions. These transition-metal-free radical chain reactions enable the efficient formation of C-C, C-S, and C-P bonds through homolytic aromatic substitution or SRN1 reactions. Moreover, the synthesis of antipsychotic drug Quetiapine was performed on gram scale through the described method. This protocol demonstrated its potential as a promising arylation method in organic synthesis.