One-pot synthesis of perfluorinated benzenedithiols from perfluoroarenes and thioacetic acid

Nikul'shin, Pavel Viktorovich; Maksimov, Alexander Mikhailovich; Gatilov, Yuriy Vasil'evich; Kovtonyuk, Vladimir Nikolaevich; Bredikhin, Roman Andreevich

doi:10.1016/j.mencom.2023.09.041

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One-pot synthesis of perfluorinated benzenedithiols from perfluoroarenes and thioacetic acid

Pavel Viktorovich Nikul'shin ^{1, 2}

Pavel Viktorovich Nikul'shin

,

Alexander Mikhailovich Maksimov ¹

Alexander Mikhailovich Maksimov

,

Yuriy Vasil'evich Gatilov ¹

Yuriy Vasil'evich Gatilov

,

Vladimir Nikolaevich Kovtonyuk ¹

Vladimir Nikolaevich Kovtonyuk

,

Roman Andreevich Bredikhin ¹

Roman Andreevich Bredikhin

¹ N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation

² A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Moscow, Russian Federation

10.1016/j.mencom.2023.09.041

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Published 2023-09-01

Communication , Volume 33, Issue 5, 721-722

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Nikul'shin P. V. et al. One-pot synthesis of perfluorinated benzenedithiols from perfluoroarenes and thioacetic acid // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 721-722.

GOST all authors (up to 50) Copy

Nikul'shin P. V., Maksimov A. M., Gatilov Y. V., Kovtonyuk V. N., Bredikhin R. A. One-pot synthesis of perfluorinated benzenedithiols from perfluoroarenes and thioacetic acid // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 721-722.

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TY - JOUR

DO - 10.1016/j.mencom.2023.09.041

UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.041

TI - One-pot synthesis of perfluorinated benzenedithiols from perfluoroarenes and thioacetic acid

T2 - Mendeleev Communications

AU - Nikul'shin, Pavel Viktorovich

AU - Maksimov, Alexander Mikhailovich

AU - Gatilov, Yuriy Vasil'evich

AU - Kovtonyuk, Vladimir Nikolaevich

AU - Bredikhin, Roman Andreevich

PY - 2023

DA - 2023/09/01

PB - Mendeleev Communications

SP - 721-722

IS - 5

VL - 33

ER -

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@article{2023_Nikul'shin,

author = {Pavel Viktorovich Nikul'shin and Alexander Mikhailovich Maksimov and Yuriy Vasil'evich Gatilov and Vladimir Nikolaevich Kovtonyuk and Roman Andreevich Bredikhin},

title = {One-pot synthesis of perfluorinated benzenedithiols from perfluoroarenes and thioacetic acid},

journal = {Mendeleev Communications},

year = {2023},

volume = {33},

publisher = {Mendeleev Communications},

month = {Sep},

url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.041},

number = {5},

pages = {721--722},

doi = {10.1016/j.mencom.2023.09.041}

}

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Nikul'shin, Pavel Viktorovich, et al. “One-pot synthesis of perfluorinated benzenedithiols from perfluoroarenes and thioacetic acid.” Mendeleev Communications, vol. 33, no. 5, Sep. 2023, pp. 721-722. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.041.

Keywords

crystal structure.

nucleophilic substitution

perfluroarenes

synthesis

thioacetic acid

thiols

Abstract

The direction of the reaction between substituted perfluorobenzenes and thioacetic acid depends on the location of the substituents in perfluoroaromatic ring. Hexafluorobenzene reacts at positions 1 and 4, perfluoro-m-xylene reacts at positions 4 and 6, while perfluoroindane reacts at positions 5 and 6 to give the corresponding dithiols with para-, meta- and ortho-location of the thiol groups, respectively. Domino-reaction of perfluoroindane-5-thiol and its acetyl thioester affords hexadecafluoro-2,12-dithia-pentacyclo[11.7.0.03,11.05,9.015,19]icosa-1(13),3,5(9),10,14,19-hexaene