Ionic Hydrogenation of α,β-Unsaturated Ketones with Cyclohexane in the Presence of Aluminum Halides Full article
| Journal |
Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393 |
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| Output data | Year: 2001, Volume: 37, Number: 11, Pages: 1534-1541 Pages count : 8 DOI: 10.1023/A:1013891616553 | ||
| Tags | STABLE CARBOCATIONS;l AROMATIC-COMPOUNDS; ACIDIC AGENTS; DERIVATIVES; DICATIONS; PHENOLS; Cyclohexane; AlCl3; Aluminum Chloride; Reaction Pattern; Ionic Hydrogenation | ||
| Authors |
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| Affiliations |
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Funding (2)
| 1 | The Ministry of Education and Science of the Russian Federation | 164/97 |
| 2 | The Ministry of Education and Science of the Russian Federation | A 0051 |
Abstract:
4-Methyl-3-penten-2-one, 3-hepten-2-one, 3-methyl-1-phenyl-2-buten-1-one, 4-(2,4-dichlorophenyl)-, 4-(4-hydroxyphenyl)-, 4-(4-methoxyphenyl)-, 4-(2-hydroxyphenyl)-, and 4-(4-dimethylaminophenyl)-3-buten-2-ones, and 3-(4-methoxyphenyl)-1-phenyl-2-propenone react with cyclohexane in the presence of excess aluminum chloride or aluminum bromide in CH2Cl2 or CH2Br2, respectively, at room temperature to form the corresponding saturated ketones in high yields. Using 4-phenyl-and 4-(4-methoxyphenyl)-3-buten-2-ones as examples, it was shown that the reaction pattern does not change in going from the Lewis acids AlCl3, and AlBr3 to proton-donor acid system CF3SO3H-SbF5. The reactive intermediates are likely to be C-protonated complexes of α,β-unsaturated ketones with aluminum halides or their O,C-diprotonated analogs.
Cite:
Koltunov K.Y.
, Repinskaya I.B.
, Borodkin G.I.
Ionic Hydrogenation of α,β-Unsaturated Ketones with Cyclohexane in the Presence of Aluminum Halides
Russian Journal of Organic Chemistry. 2001. V.37. N11. P.1534-1541. DOI: 10.1023/A:1013891616553 WOS Scopus РИНЦ ANCAN OpenAlex
Ionic Hydrogenation of α,β-Unsaturated Ketones with Cyclohexane in the Presence of Aluminum Halides
Russian Journal of Organic Chemistry. 2001. V.37. N11. P.1534-1541. DOI: 10.1023/A:1013891616553 WOS Scopus РИНЦ ANCAN OpenAlex
Original:
Колтунов К.Ю.
, Репинская И.Б.
, Бородкин Г.И.
Ионное гидрирование α,β-кетонов циклогексаном в присутствии галогенидов алюминия.
Журнал органической химии. 2001. Т.37. №11. С.1610-1617.
Ионное гидрирование α,β-кетонов циклогексаном в присутствии галогенидов алюминия.
Журнал органической химии. 2001. Т.37. №11. С.1610-1617.
Dates:
| Submitted: | Jul 10, 2000 |
| Published print: | Nov 1, 2001 |
Identifiers:
| Web of science: | WOS:000174149200004 |
| Scopus: | 2-s2.0-0035497924 |
| Elibrary: | 13384741 |
| Chemical Abstracts: | 2002:200708 |
| Chemical Abstracts (print): | 137:20055 |
| OpenAlex: | W2950280773 |