92-85-3Relevant articles and documents
Isotopically Selective Electron Transfer between Free Radical Cations and their Parent Molecules Enables Isotope Enrichment
Liu, Zhong-Li,Lu, Jian-Min,Chen, Pin,Wang, Xi-Lu,Wen, Xiao-Lin,et al.
, p. 76 - 77 (1992)
Electron transfer between the thianthrene radical cation and its neutral molecule precursor shows a significant H/D equilibrum isotope effect which may be used for isotopic enrichment.
Regio- and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles
Berger, Florian,Chen, Junting,Li, Jiakun,Plutschack, Matthew B.,Ritter, Tobias
, p. 5616 - 5620 (2020)
Herein, we report a regioselective alkenyl electrophile synthesis from unactivated olefins that is based on a direct and regioselective C?H thianthrenation reaction. The selectivity is proposed to arise from an unusual inverse-electron-demand hetero-Diels–Alder reaction. The alkenyl sulfonium salts can serve as electrophiles in palladium- and ruthenium-catalyzed cross-coupling reactions to make alkenyl C?C, C?Cl, C?Br, and C?SCF3 bonds with stereoretention.
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Gilman,Swayampati
, p. 2163 (1956)
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Synthesis of 1- and 2-substituted thianthrenes
Lovell, James M.,Joule, John A.
, p. 2391 - 2395 (1996)
Lithiation of thianthrene at C-1 allows the synthesis of various 1-substituted thianthrenes for example thianthren-1-ylboronic acid and 1-tributylstannylthianthrene, which undergo palladium-catalysed couplings with aryl halides. 2-Bromothianthrene provides an entry to 2-substituted thianthrenes via lithium-halogen exchange then reaction of 2-lithiothianthrene with electrophiles including formation of the 2-boronic acid and 2-tributylstannylthianthrene which were coupled to aryl halides.
2,3,8,9-Dibenzo-5,6-(substituted)benzo-1,4-dithio-7-azacyclonona-2,5,8- trienes. Synthesis and Mechanistic Study
Kim, Kyongtae,Kim, Man Nyoung
, p. 1 - 12 (1997)
5-(2-Acetamidoaryl)thianthreniumyl perchlorates reacted with potassium hydroxide in methanol at reflux giving 2,3,8,9-dibenzo-5,6-(substituted)benzo-1,4-dithio-7-azacyclonona-2,5,8-trienes 4 in 43 to 75% yields, whereas the reactions of the same compounds with sodium hydride in the absence or in the presence of dimethyl sulfate in refluxing tetrahydrofuran gave N-acetylated and N-methylated 4 in 68 to 96% and 27 to 56% yields, respectively. The mechanism of the formation of the products might be explained by a nucleophilic attack of amide ions 10, 12, and 14 at the ispo-position of the thianthrene ring. A sulfuranyl radical mechanism might be involved in these reactions.
Addition of Thianthrene Cation Radical to Cycloalkenes. An Unexpected Monoadduct
Lee, Wang Keun,Liu, Bo,Park, Chan Won,Shine, Henry J.,Guzman-Jimenez, Ilse Y.,Whitmire, Kenton H.
, p. 9206 - 9210 (1999)
Whereas the addition of thianthrene cation radical perchlorate (Th?+ClO4-) to cyclohexene gives a bisadduct, namely, trans-1,2-bis(5-thianthreniumyl)cyclohexane diperchlorate (1), and additon to other alkenes and alkynes also gives trans-bisadducts, addition to cyclooctene gave only a cis-monoadduct, namely, 1,2-(5,10-thianthreniumdiyl)cyclooctane diperchlorate (2a). Similar monoadducts 2b-d were obtained from the addition of Th?+BF4-, Th?+SbF6-, and Th?+PF6- to cyclooctene. The structure of the monoadduct was deduced from its 1H and 13C NMR spectra, from the stoichiometry of its formation, and from the stoichiometry of its reaction with NaSPh, which gave equimolar amounts of cyclooctene, thianthrene, and diphenyl disulfide. The structure was confirmed with X-ray crystallography. Addition of Th?+ salts to cyclopentene and cycloheptene gave mixtures of mono- and bisadducts. The bisadduct of Th?+SbF6- to cyclopentene, separated from the small amount of monoadduct by crystallization, was shown with X-ray crystallography to have the trans configuration.
Allylic Amination of Alkenes with Iminothianthrenes to Afford Alkyl Allylamines
Chen, Junting,Cheng, Qiang,Lin, Songyun,Ritter, Tobias
, p. 17287 - 17293 (2020/11/02)
Allylic C-H amination is currently accomplished with (sulfon)amides or carbamates. Here we show the first allylic amination that can directly afford alkyl allylamines, enabled by the reactivity of thianthrene-based nitrogen sources that can be prepared from primary amines in a single step.
Dechalcogenization of Aryl Dichalcogenides to Synthesize Aryl Chalcogenides via Copper Catalysis
Cao, Fei,Chen, Jinhong,Deng, Jiedan,Deng, Xuemei,Hou, Yongsheng,Shao, Xiangfeng,Shi, Tao,Wang, Yongqiang,Wang, Zhen,Wu, Lingxi,Yang, Jinru,Yang, Yuhang
, p. 2707 - 2712 (2020/03/11)
An application for dechalcogenization of aryl dichalcogenides via copper catalysis to synthesize aryl chalcogenides is disclosed. This approach is highlighted by the practical conditions, broad substrate scope, and good functional group tolerance with several sensitive groups such as aldehyde, ketone, ester, amide, cyanide, alkene, nitro, and methylsulfonyl. Furthermore, the robustness of this methodology is depicted by the late-stage modification of estrone and synthesis of vortioxetine. Remarkably, synthesis of more challenging organic materials with large ring tension under milder conditions and synthesis of some halogen contained diaryl sulfides which could not be synthesized using metal-catalyzed coupling reactions of aryl halogen are successfully accomplished with this protocol.
