Electrophilic amination of methylbenzenes with the system NaN3-AlCl3-HCl. Effects of the solvent, crown ether, and substrate structure 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: 2003, Volume: 39, Number: 5, Pages: 672-679 Pages count : 8 DOI: 10.1023/A:1026057212359 | ||||
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Abstract:
Using mesitylene and o-xylene as examples, it was shown that the solvent nature strongly affects the conversion of methylbenzenes in electrophilic amination with the system NaN3-AlCl3-HCl. Two-parameter correlations were found between the substrate conversion, on the one hand, and dielectric constant and number of heavy atoms in the solvent, on the other. A considerable solvent effect on the regioselectivity of amination of o-xylene was observed. The presence of 18-crown-6 weakly affects the ratio of isomeric amines, but the conversion of o-xylene sharply decreases. Solid aromatic substrates, such as durene and pentamethylbenzene can also be involved in electrophilic amination with the system NaN3-AlCl3-HCl. On the basis of the experimental data and the results of quantum-chemical calculations, participation of a nitrenium intermediate in this reaction was postulated.
Cite:
Borodkin G.
, Elanov I.
, Popov S.
, Pokrovskii L.
, Shubin V.
Electrophilic amination of methylbenzenes with the system NaN3-AlCl3-HCl. Effects of the solvent, crown ether, and substrate structure
Russian Journal of Organic Chemistry. 2003. V.39. N5. P.672-679. DOI: 10.1023/A:1026057212359 WOS Scopus РИНЦ OpenAlex
Electrophilic amination of methylbenzenes with the system NaN3-AlCl3-HCl. Effects of the solvent, crown ether, and substrate structure
Russian Journal of Organic Chemistry. 2003. V.39. N5. P.672-679. DOI: 10.1023/A:1026057212359 WOS Scopus РИНЦ OpenAlex
Original:
Бородкин Г.И.
, Еланов И.Р.
, Попов С.А.
, Покровский Л.М.
, Шубин В.Г.
Электрофильное аминирование метилбензолов системой nan 3-alcl 3-hcl. эффекты структуры, растворителя и краун-эфира
Журнал органической химии (RUSS J ORG CHEM+). 2003. Т.39. №5. С.718-724. РИНЦ
Электрофильное аминирование метилбензолов системой nan 3-alcl 3-hcl. эффекты структуры, растворителя и краун-эфира
Журнал органической химии (RUSS J ORG CHEM+). 2003. Т.39. №5. С.718-724. РИНЦ
Identifiers:
| Web of science: | WOS:000185779100011 |
| Scopus: | 2-s2.0-1642491910 |
| Elibrary: | 13431070 |
| OpenAlex: | W349867138 |