Heat-Induced Reactions of 6-Bromo-, 6-Chloro-, and 6-(Methylsulfanyl)octafl uoroindane-5-thiols with Tetrafluoroethylene. Synthesis of Dodecafluoro-2H,3H,5H,6H,7H-indeno[5,6-b]thiophene
- Authors: Nikul’shin P.V.1, Maksimov A.M.1, Gatilov Y.V.1, Platonov V.E.1
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Affiliations:
- N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
- Issue: Vol 89, No 12 (2019)
- Pages: 2378-2385
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/223193
- DOI: https://doi.org/10.1134/S1070363219120090
- ID: 223193
Cite item
Abstract
Dodecafluoro-2H,3H,5H,6H,7H-indeno[5,6-b]thiophene has been synthesized as the major product of co-pyrolysis of 6-bromo-, 6-chlorooctafluoroindane-5-thiols, or bis(6-bromo-5-perfluoroindanyl)disulfane with tetrafluoroethylene under flow conditions at 400-625ºC, along with small amount of tetradecafluoro-1,2,3,5,6,7-hexahydro-s-indacene. Dodecafluoro-2H,3H,5H,6H,7H-indeno[5,6-b]thiophene formed in the reaction of 6-(meth-ylsulfanyl)octafluoroindane-5-thiol with tetrafluoroethylene at 420ºC has been isolated, and its structure has been confirmed by X-ray diffraction analysis. The schemes of the products formation involving intermediate radicals have been proposed.
About the authors
P. V. Nikul’shin
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
Email: platonov@nioch.nsc.ru
Russian Federation, Novosibirsk, 630090
A. M. Maksimov
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
Email: platonov@nioch.nsc.ru
Russian Federation, Novosibirsk, 630090
Yu. V. Gatilov
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
Email: platonov@nioch.nsc.ru
Russian Federation, Novosibirsk, 630090
V. E. Platonov
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
Author for correspondence.
Email: platonov@nioch.nsc.ru
Russian Federation, Novosibirsk, 630090