Preparation of a Stable Diaryl Trisulfide from a Sacrificial Sulfur Cathode and 2-Chloropyrimidine.

Genesty, Marc; Pommatau, Gilles; Degrand, Chantal; Fang, Weihua; Tang, Wen-Zhang; Song, Lian-Huan; Chen, Wen-Kui; Toftlund, Hans

doi:10.3891/acta.chem.scand.53-0952

Acta Chem. Scand.

1999

DOI: 10.3891/acta.chem.scand.53-0952

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Preparation of a Stable Diaryl Trisulfide from a Sacrificial Sulfur Cathode and 2-Chloropyrimidine.

Marc Genesty¹,

Gilles Pommatau²,

Chantal Degrand³

et al.

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1,5,2,4,6,8-Dithiatetrazocine. Synthesis, computation, crystallography and voltammetry of the parent heterocycle

Moock¹,

Wong

Boeré

2011

Dalton Trans.

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The prototypal 1,5,2,4,6,8-dithiatetrazocine has been synthesized for the first time by two routes: reaction of 1,2,3,5-dithiadiazolium chloride with N,N,N'-tris(trimethylsilyl)formamidine in acetonitrile and reaction of 1,2,3,5-dithiadiazolyl radical with dioxygen in solution. Yields are low but single crystals could be obtained for an X-ray crystal structure determination which shows it to have the planar delocalized structure predicted by B3LYP/6-311+G(2d,p) hybrid DFT calculations. The crystal structure is strongly reminiscent of that of benzene in the same Pbca space group. Aromaticity is demonstrated by a (1)H NMR chemical shift of +9.70 ppm indicative of diamagnetic ring shielding and an intense low-energy optical absorption with λ(max) = 349 nm (MeOH). The voltammetric behaviour of the title compound is compared with that of 1,3λ(4)δ(2),5,2,4-trithiadiazepine; both resist electrochemical oxidation and reduction over a wide potential range as is typical for aromatic heterocycles.

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1,5,2,4,6,8-Dithiatetrazocine. Synthesis, computation, crystallography and voltammetry of the parent heterocycle

Moock¹,

Wong

Boeré

2011

Dalton Trans.

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Photoinduced Electron Transfer Reactions in Heterocyclic Chemistry

Fagnoni¹

2003

HETEROCYCLES

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Preparation of a Stable Diaryl Trisulfide from a Sacrificial Sulfur Cathode and 2-Chloropyrimidine.

Cited by 2 publications

References 0 publications

1,5,2,4,6,8-Dithiatetrazocine. Synthesis, computation, crystallography and voltammetry of the parent heterocycle

1,5,2,4,6,8-Dithiatetrazocine. Synthesis, computation, crystallography and voltammetry of the parent heterocycle

Photoinduced Electron Transfer Reactions in Heterocyclic Chemistry

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