1212-08-4Relevant articles and documents
Electrochemical oxidative cyclization of activated alkynes with diselenides or disulfides: Access to functionalized coumarins or quinolinones
Hua, Jiawei,Fang, Zheng,Xu, Jia,Bian, Mixue,Liu, ChengKou,He, Wei,Zhu, Ning,Yang, Zhao,Guo, Kai
, p. 4706 - 4711 (2019)
A direct electrochemical oxidative cyclization of alkynoates and alkynamides with diselenides or disulfides for the synthesis of coumarins and quinolinones bearing a chalcogen functional group has been developed. This green and efficient approach was realized through a constant current electrolysis in an undivided cell under metal-free and oxidant-free conditions. Moreover, a series of selenium/sulfur-substituted coumarin and quinolinone products were obtained in moderate to good yields with a broad scope and functional group tolerance.
A Facile Diastereoselective Synthesis of Functionalized 1,2,3-Trisubstituted Benzocyclopentenes through the Cycloaddition of Bis(phenylsulfonyl)iodonium Ylides to Cyclic Alkenes
Adam, Waldemar,Gogonas, Efstathios P.,Hadjiarapoglou, Lazaros P.
, p. 9155 - 9158 (2003)
The thermal cycloaddition of β-disulfonyl iodonium ylides to cyclic alkenes affords exclusively 1,2,3-trisubstituted cis(1,2)/cis(2,3)-configured benzocyclopentenes by an electrophilic attack of the ylide on the olefinic double bond. This unsual transformation provides a convenient and direct method for the diastereoselective synthesis of functionalized bicyclo [3.3.0] octanes (characteristic structural units contained in polyquinane natural products), when cyclopentenes are used as cycloalkene partner.
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Barnard
, p. 4673 (1957)
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Edmondson et al.
, p. 618 (1971)
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Oxidation of organic sulfides and disulfides with a tert-butyl hydroperoxide-aluminum tri-tert-butoxide system
Zaburdaeva,Dodonov
, p. 185 - 187 (2011)
Methyl phenylethynyl and phenyl phenylethynyl sulfides are selectively converted into methyl phenylethynyl and phenyl phenylethynyl sulfones, respectively, under the action of system tert-butyl hydroperoxide-aluminum tri-tert-butoxide in benzene at 20 °C. The analogous oxidation of diphenyl disulfide results in S-phenyl benzenethiosulfonate.
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Ju,T.-L. et al.
, p. 610 - 614 (1979)
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Metal-free oxidation of sulfides by carbon nitride with visible light illumination at room temperature
Zhang, Pengfei,Wang, Yong,Li, Haoran,Antonietti, Markus
, p. 1904 - 1908 (2012)
Mesoporous graphitic carbon nitride (mpg-C3N4) has been developed as a non-metal, heterogeneous photocatalyst for the selective oxidation of sulfides to sulfoxides with O2 at room temperature. Especially, the combination of mpg-C3N4 and aldehydes was a highly active system under visible-light irradiation. For example, mpg-C 3N4/isobutyraldehyde catalytic oxidation of methyl phenyl sulfide afforded 97% conversion with 98% selectivity for the methyl phenyl sulfoxide in 4 h. Moreover, the mpg-C3N4 can be easily recovered by filtration and then reused at least four times without losing activity. By exploring the electron spin resonance and some comparative experiments, a catalytic mechanism of this oxidation was provided. Finally, the system also works well in the oxidation of a number of sulfides, including sulfides bearing various groups, and phenyl disulfide. The use of a metal-free heterogeneous catalyst and visible light energy, along with the mild reaction conditions makes this oxidation reaction an environmentally benign and energy-saving chemical process. The Royal Society of Chemistry 2012.
Scalable Synthesis of S-Fluoromethyl Benzenesulfonothioate
Chen, Wenbo,Lu, Long,Shen, Qilong,Yao, Ruichao,Zhao, Qunchao
, p. 1090 - 1094 (2020)
A general and practical method for the preparation of S-fluoromethyl benzenesulfonothioate on a 500 g scale in two steps from readily available CH2FCl, sulfur, and sodium benzenesulfinate is reported. The reaction was found to be rather sensitive to water and temperature. Furthermore, the main side product of the reaction was identified to be S-phenyl benzenesulfonothioate.
Chemichal Ionization and Electron Impact Mass Spectra of Thiosulfinates, Thiosulfonates, and Sulfinyl Sulfones
Freeman, Fillmore,Angeletakis, Christos N.
, p. 114 - 122 (1982)
The chemical ionization and electron impact mass spectra of some thiosulfinates, thiosulfonates, and sulfinyl sulfones have been studied.The electron impact mass spectra of four of the six thiosulfonates show molecular ions of less than 1percent.Inconclusive evidence was obtained for sulfenyl sulfinate type intermediates in the electron impact spectra of thiosulfonates.The electron impact spectra of thiosulfonates were similar to those of thiosulfonates.The chemical ionization (isobutane) mass spectra of thiosulfinates and thiosulfonatesgenerally show protonated molecular ions (+) as base peaks and (+) and (+) peaks.
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Abe,Tsurugi
, p. 441 (1972)
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A new synthesis of thioesters and selenoesters of triflic acid under oxidative conditions
Billard, Thierry,Langlois, Bernard R.
, p. 63 - 64 (1997)
Trifluoromethanethio-(or seleno-)sulfonates (CF3SO2YR, Y=S, Se) are easily obtained in one step at 0-20 °C from disulfides (or diselenides), sodium trifluoromethanesulfinate and [bis-(trifluoroacetoxy)iodo]benzene (BTIB).
Visible-Light-Induced Cyclization/Aromatization of 2-Vinyloxy Arylalkynes: Synthesis of Thio-Substituted Dibenzofuran Derivatives
Chen, Hui,Chen, Yanyan,Mo, Zuyu,Xu, Yanli,Yan, Yunyun,Zhang, Niuniu
supporting information, p. 376 - 381 (2021/01/13)
A visible-light-induced cascade reaction of 2-vinyloxy arylalkynes with thiosulfonates was developed and provided unexpected thio-substituted dibenzofuran derivatives in moderate yields. Mechanistic studies revealed the thiosulfonylation product of 2-vinyloxy arylalkyne was the key intermediate, and the additive disulfide played the role of hydrogen abstraction in the aromatization process to offer the desired product. This reaction presents a new reaction mode for the construction of polycyclic oxygen heterocycles.
Synthesis of Symmetrical and Unsymmetrical Thiosulfonates from Disulfides through Electrochemically Induced Disulfide Bond Metathesis and Site-Selective Oxidation
Hilt, Gerhard,Strehl, Julia
supporting information, (2021/10/14)
The anodic generation of symmetrical and unsymmetrical thiosulfonates is presented. First, the oxidation of disulfides yielding symmetrical thiosulfonates was realized. The direct synthesis is performed using a simple quasi-divided cell design, whereby using a supporting electrolyte is unnecessary. Its principle was then expanded to the conversion of unsymmetrical disulfides that were generated in situ through metathesis of two symmetrical disulfides. This enables a direct access to unsymmetrical thiosulfonates without any pre-functionalization or elaborate synthesis of the starting materials for the first time. The reaction scope was investigated by converting differently functionalized aliphatic and aromatic disulfides in moderate to very good yields. Furthermore, a sensitivity assessment for an improved reproducibility and a robustness screen to determine the compatibility of the reaction against functional groups were performed.
