Reaction of 4-Substituted 1-[(Difluoromethyl)sulfinyl]-2,3,4,5-tetrafluorobenzenes with Ammonia and Methylamine Full article
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Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393 |
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| Output data | Year: 2020, Volume: 56, Number: 11, Pages: 1911-1919 Pages count : 9 DOI: 10.1134/S1070428020110044 | ||
| Tags | polyfluoroarenes; sulfoxides; nucleophilic aromatic substitution; ammonia; methylamine | ||
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Abstract:
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.
Cite:
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
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
ArticleLinkType.TRANSLATED_TO_ORIGINAL:
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
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
Dates:
| Published print: | Nov 1, 2020 |
| Published online: | Jan 25, 2021 |
Identifiers:
| Web of science | WOS:000607144000004 |
| Scopus | 2-s2.0-85099110491 |
| Elibrary | 45018051 |
| OpenAlex | W3119020399 |