Abstract: The interactions of N-pentafluorophenylcarbonimidoyl dichloride, N-pentafluorophenylbenzimidoyl chloride and N-pentafluorophenyl (C-pentafluorophenyl) imidoyl chloride with the S-nucleophilic reagents thiourea, sodium N,N-diethyldithiocarbamate, thiocarbonyl difluoride and bis(trifluoromethyl)trithiocarbonate in the presence of CsF or AgSCF3, or thiophenol and polyfluorinated thiophenols in the presence of anhydrous K2CO3, were studied. Reactions with charged S-nucleophiles and with S-nucleophiles in the presence of a base proceeded with preservation of the N=C multiple bond in the reaction products. By varying the reaction conditions in the case of N-pentafluorophenylcarbonimidoyl dichloride it was possible to substitute one or two chlorines and obtain mono- or di-thioimidates. When C6F5 or SC6F5 groups were present at the C atom of the N=C multiple bond, preferential substitution of the para-fluorine atom occurred. Semiempirical PM3 calculation data were used to explain the direction of these reactions. N-Pentafluorophenylcarbonimidoyl dichloride reacted with sodium N,N-diethyldithiocarbamate or thiourea to give pentafluorophenylisothiocyanate. Depending on the conditions of the reactions of polyfluorinated benzimidoyl chlorides with thiourea, N-pentafluorophenylthioamides and 2-aryl-4,5,6,7-tetrafluorobenzothiazoles were formed. An attempt to produce SCF3 derivatives from AgSCF3 was unsuccessful.

Cite: Petrova T.D. , Platonov V.E. , Shchegoleva L.N. , Maksimov A.M. , Haas A. , Schelvis M. , Lieb M.
Reactions of polyfluoroaromatic imidoyl chloride derivatives with S-nucleophilic reagents
Journal of Fluorine Chemistry. 1996. V.79. N1. P.13-25. DOI: 10.1016/0022-1139(96)03465-3 WOS Scopus

Dates:

Published print:

Jul 1, 1996

Identifiers:

Web of science	WOS:A1996VH42400004
Scopus	2-s2.0-0030188152
OpenAlex	W2953290704

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