P. V. Nikul'shin, A. M. Maksimov, Yu. V. Gatilov, V. N. Kovtonyuk, R. A. Bredikhin, “One-pot synthesis of perfluorinated benzenedithiols from perfluoroarenes and thioacetic acid”, Mendeleev Commun., 2023, Volume 33, Issue 5,Pages <nobr>721

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Communications

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

P. V. Nikul'shin^ab, A. M. Maksimov^a, Yu. V. Gatilov^a, V. N. Kovtonyuk^a, R. A. Bredikhin^a

^a N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation
^b A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Moscow, Russian Federation

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[11.7.0.0^3,11.0^5,9.0^15,19]icosa-1(13),3,5(9),10,14,19-hexaene

Keywords: perfluroarenes, thioacetic acid, nucleophilic substitution, thiols, synthesis, crystal structure.

Language: English

DOI: 10.1016/j.mencom.2023.09.041

	*Supplementary materials:*
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