Reaction of 4-Substituted 1-[(Difluoromethyl)sulfinyl]-2,3,4,5-tetrafluorobenzenes with Ammonia and Methylamine

Reaction of 4-Substituted 1-[(Difluoromethyl)sulfinyl]-2,3,4,5-tetrafluorobenzenes with Ammonia and Methylamine Научная публикация

Журнал

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Вых. Данные

Год: 2020, Том: 56, Номер: 11, Страницы: 1911-1919 Страниц : 9 DOI: 10.1134/S1070428020110044

Ключевые слова

polyfluoroarenes; sulfoxides; nucleophilic aromatic substitution; ammonia; methylamine

Авторы

Koshcheev B.V. ¹ , Maksimov A.M. ¹ , Platonov V.E. ¹ , Bredikhin R.A. ¹

Организации

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

The reaction of 4-X-substituted 1-[(difluoromethyl)sulfinyl]-2,3,5,6-tetrafluorobenzenes (X = CF3, H, OMe) with methylamine and ammonia in MeCN, Et2O, and hydrocarbons occurs involves nucleophilic substitution in position 2 of the substrate. The reaction time increases with increasing donor ability of substituent X in the series X = CF3 < H < OMe, as well as with decreasing solvent polarity. Further substitution of fluorine in position 6 of the substrate by methylamine is also possible, but requires a higher reaction temperature. The reaction of ammonia with 1-[(difluoromethyl)sulfinyl]-4-methoxy-2,3,5,6-tetrafluorobenzene is accompanied by partial demethylation to form 2-[(difluoromethyl)sulfinyl]-3,4,6-trifluoro-5-methoxy-N-methylaniline and 4-[(difluoromethyl)sulfinyl]-2,3,5,6-tetrafluorophenol.

Koshcheev B.V. , Maksimov A.M. , Platonov V.E. , Bredikhin R.A.
Reaction of 4-Substituted 1-[(Difluoromethyl)sulfinyl]-2,3,4,5-tetrafluorobenzenes with Ammonia and Methylamine
Russian Journal of Organic Chemistry. 2020. V.56. N11. P.1911-1919. DOI: 10.1134/S1070428020110044 WOS Scopus РИНЦ OpenAlex

Кощеев Б.В. , Максимов А.М. , Платонов В.Е. , Бредихин Р.А.
ВЗАИМОДЕЙСТВИЕ 4-ЗАМЕЩЕННЫХ 1-[(ДИФТОРМЕТИЛ)СУЛЬФИНИЛ]-2,3,5,6-ТЕТРАФТОРБЕНЗОЛОВ С АММИАКОМ И МЕТИЛАМИНОМ
Журнал органической химии (RUSS J ORG CHEM+). 2020. Т.56. №11. С.1700-1709.. DOI: 10.31857/S051474922011004X РИНЦ OpenAlex

Опубликована в печати:	1 нояб. 2020 г.
Опубликована online:	25 янв. 2021 г.

Web of science:	WOS:000607144000004
Scopus:	2-s2.0-85099110491
РИНЦ:	45018051
OpenAlex:	W3119020399

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