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Substitution of a Fluorine Atom in Perfluorobenzonitrile by a Lithiated Nitronyl Nitroxide. / Tretyakov, Evgeny V.; Fedyushin, Pavel A.; Panteleeva, Elena V. et al.

In: Journal of Organic Chemistry, Vol. 82, No. 8, 21.04.2017, p. 4179-4185.

Research output: Contribution to journalArticlepeer-review

Harvard

Tretyakov, EV, Fedyushin, PA, Panteleeva, EV, Stass, DV, Bagryanskaya, IY, Beregovaya, IV & Bogomyakov, AS 2017, 'Substitution of a Fluorine Atom in Perfluorobenzonitrile by a Lithiated Nitronyl Nitroxide', Journal of Organic Chemistry, vol. 82, no. 8, pp. 4179-4185. https://doi.org/10.1021/acs.joc.7b00144

APA

Tretyakov, E. V., Fedyushin, P. A., Panteleeva, E. V., Stass, D. V., Bagryanskaya, I. Y., Beregovaya, I. V., & Bogomyakov, A. S. (2017). Substitution of a Fluorine Atom in Perfluorobenzonitrile by a Lithiated Nitronyl Nitroxide. Journal of Organic Chemistry, 82(8), 4179-4185. https://doi.org/10.1021/acs.joc.7b00144

Vancouver

Tretyakov EV, Fedyushin PA, Panteleeva EV, Stass DV, Bagryanskaya IY, Beregovaya IV et al. Substitution of a Fluorine Atom in Perfluorobenzonitrile by a Lithiated Nitronyl Nitroxide. Journal of Organic Chemistry. 2017 Apr 21;82(8):4179-4185. doi: 10.1021/acs.joc.7b00144

Author

Tretyakov, Evgeny V. ; Fedyushin, Pavel A. ; Panteleeva, Elena V. et al. / Substitution of a Fluorine Atom in Perfluorobenzonitrile by a Lithiated Nitronyl Nitroxide. In: Journal of Organic Chemistry. 2017 ; Vol. 82, No. 8. pp. 4179-4185.

BibTeX

@article{2e890214fef8497dab158b94eef0ebf7,
title = "Substitution of a Fluorine Atom in Perfluorobenzonitrile by a Lithiated Nitronyl Nitroxide",
abstract = "A 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl (1) lithium derivative was found to react with perfluorobenzonitrile (2) substituting its para-fluorine atom to form 2-(4-cyanotetrafluorophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl (3), a new nitronyl nitroxide containing a multifunctional framework of strong electron-withdrawing nature. This result shows the possibility of obtaining multifunctional nitronyl nitroxides via the interaction of paramagnetic lithium derivatives as C-nucleophiles with polyfluoroarenes activated for nucleophilic substitution. The reaction regioselectivity is supported by the data of quantum-chemical calculations, which also show that the reaction follows a concerted pathway without formation of an intermediate. Reduction of nitronyl nitroxide 3 in system NaNO2-AcOH yielded corresponding iminonitroxide 4. Characterization of persistent radicals 3 and 4 obtained by the SNF synthetic strategy includes X-ray crystal structures, electron spin resonance data, and static magnetic-susceptibility measurements. X-ray diffraction analysis of both nitronyl nitroxide and iminonitroxide revealed a complete match of the parameters of their crystal lattices.",
keywords = "NUCLEOPHILIC AROMATIC-SUBSTITUTION, BETA-AMINOCINNAMONITRILES, DERIVATIVES, INHIBITORS, RADICALS, SYSTEMS, AGENTS",
author = "Tretyakov, {Evgeny V.} and Fedyushin, {Pavel A.} and Panteleeva, {Elena V.} and Stass, {Dmitri V.} and Bagryanskaya, {Irina Yu} and Beregovaya, {Irina V.} and Bogomyakov, {Artem S.}",
year = "2017",
month = apr,
day = "21",
doi = "10.1021/acs.joc.7b00144",
language = "English",
volume = "82",
pages = "4179--4185",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "8",

}

RIS

TY - JOUR

T1 - Substitution of a Fluorine Atom in Perfluorobenzonitrile by a Lithiated Nitronyl Nitroxide

AU - Tretyakov, Evgeny V.

AU - Fedyushin, Pavel A.

AU - Panteleeva, Elena V.

AU - Stass, Dmitri V.

AU - Bagryanskaya, Irina Yu

AU - Beregovaya, Irina V.

AU - Bogomyakov, Artem S.

PY - 2017/4/21

Y1 - 2017/4/21

N2 - A 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl (1) lithium derivative was found to react with perfluorobenzonitrile (2) substituting its para-fluorine atom to form 2-(4-cyanotetrafluorophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl (3), a new nitronyl nitroxide containing a multifunctional framework of strong electron-withdrawing nature. This result shows the possibility of obtaining multifunctional nitronyl nitroxides via the interaction of paramagnetic lithium derivatives as C-nucleophiles with polyfluoroarenes activated for nucleophilic substitution. The reaction regioselectivity is supported by the data of quantum-chemical calculations, which also show that the reaction follows a concerted pathway without formation of an intermediate. Reduction of nitronyl nitroxide 3 in system NaNO2-AcOH yielded corresponding iminonitroxide 4. Characterization of persistent radicals 3 and 4 obtained by the SNF synthetic strategy includes X-ray crystal structures, electron spin resonance data, and static magnetic-susceptibility measurements. X-ray diffraction analysis of both nitronyl nitroxide and iminonitroxide revealed a complete match of the parameters of their crystal lattices.

AB - A 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl (1) lithium derivative was found to react with perfluorobenzonitrile (2) substituting its para-fluorine atom to form 2-(4-cyanotetrafluorophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl (3), a new nitronyl nitroxide containing a multifunctional framework of strong electron-withdrawing nature. This result shows the possibility of obtaining multifunctional nitronyl nitroxides via the interaction of paramagnetic lithium derivatives as C-nucleophiles with polyfluoroarenes activated for nucleophilic substitution. The reaction regioselectivity is supported by the data of quantum-chemical calculations, which also show that the reaction follows a concerted pathway without formation of an intermediate. Reduction of nitronyl nitroxide 3 in system NaNO2-AcOH yielded corresponding iminonitroxide 4. Characterization of persistent radicals 3 and 4 obtained by the SNF synthetic strategy includes X-ray crystal structures, electron spin resonance data, and static magnetic-susceptibility measurements. X-ray diffraction analysis of both nitronyl nitroxide and iminonitroxide revealed a complete match of the parameters of their crystal lattices.

KW - NUCLEOPHILIC AROMATIC-SUBSTITUTION

KW - BETA-AMINOCINNAMONITRILES

KW - DERIVATIVES

KW - INHIBITORS

KW - RADICALS

KW - SYSTEMS

KW - AGENTS

UR - http://www.scopus.com/inward/record.url?scp=85018509951&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.7b00144

DO - 10.1021/acs.joc.7b00144

M3 - Article

C2 - 28358985

AN - SCOPUS:85018509951

VL - 82

SP - 4179

EP - 4185

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 8

ER -

ID: 9032709