Synthesis of Nitromethyl Derivatives from Sulfur-Containing Pentafluorobenzenes

Synthesis of Nitromethyl Derivatives from Sulfur-Containing Pentafluorobenzenes Full article

Journal

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

Output data

Year: 2022, Volume: 58, Number: 9, Pages: 1242-1249 Pages count : 8 DOI: 10.1134/s107042802209007x

Tags

sulfur-containing polyfluoroarenes nitromethane nitromethyl derivatives nucleophilic aromatic substitution

Authors

Koshcheev B.V. ¹ , Maksimov A.M. ¹

Affiliations

1	Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences

The reaction of methyl- and (difluoromethyl)sulfanyl-, methane- and difluoromethanesulfinyl-, and methane- and difluoromethanesulfonylpentafluorobenzenes with nitromethane in the presence of 1,8diazabicyclo[5.4.0]undec-7-ene (DBU) in diethyl ether involved replacement of fluorine at the para position of the aromatic ring with the formation of the corresponding nitromethyl derivatives. The reaction temperature decreased in parallel with increase of the electron-withdrawing power of the sulfur-containing substituent. Treatment of 1,2,4,5-tetrafluoro-3-(methylsulfanyl)-6-(nitromethyl)benzene with sodium methoxide afforded the corresponding aci-nitro salt.

Koshcheev B.V. , Maksimov A.M.
Synthesis of Nitromethyl Derivatives from Sulfur-Containing Pentafluorobenzenes
Russian Journal of Organic Chemistry. 2022. V.58. N9. P.1242-1249. DOI: 10.1134/s107042802209007x WOS РИНЦ

Кощеев Б.В. , Максимов А.М.
Получение нитрометильных производных из серосодержащих пентафторбензолов
Журнал органической химии (RUSS J ORG CHEM+). 2022. Т.58. №9. С.985-993. DOI: 10.31857/S0514749222090075 РИНЦ

Submitted:	Dec 14, 2021
Accepted:	Dec 31, 2021
Published online:	Nov 1, 2022

Web of science	WOS:000877715800007
Elibrary	53708409
OpenAlex	W4312360273