Reactions of polyfluoroaromatic imidoyl chloride derivatives with S-nucleophilic reagents Научная публикация
| Журнал |
Journal of Fluorine Chemistry
ISSN: 0022-1139 |
||||
|---|---|---|---|---|---|
| Вых. Данные | Год: 1996, Том: 79, Номер: 1, Страницы: 13-25 Страниц : 13 DOI: 10.1016/0022-1139(96)03465-3 | ||||
| Ключевые слова | reactions; polyfluoroaromatic imidoyl chloride derivatives; S-nucleophilic reagents; NMR spectroscopy; IR spectroscopy; semiempirical calculations | ||||
| Авторы |
|
||||
| Организации |
|
Реферат:
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.
Библиографическая ссылка:
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 OpenAlex
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 OpenAlex
Даты:
| Опубликована в печати: | 1 июл. 1996 г. |
Идентификаторы БД:
| Web of science: | WOS:A1996VH42400004 |
| Scopus: | 2-s2.0-0030188152 |
| OpenAlex: | W2953290704 |