Ketonization of 1,5-Cyclooctadiene by Nitrous Oxide Научная публикация
| Журнал |
Advanced Synthesis and Catalysis
ISSN: 1615-4150 , E-ISSN: 1615-4169 |
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| Вых. Данные | Год: 2009, Том: 351, Номер: 11-12, Страницы: 1905-1911 Страниц : 6 DOI: 10.1002/adsc.200900278 | ||
| Ключевые слова | 1,3-dipolar cycloadditions, 1,5-cyclooctadiene, Cyclooctanediones, Ketonization, Nitrous oxide, Oxidation | ||
| Авторы |
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| Организации |
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Реферат:
The kinetics and mechanism of the liquid phase ketonization of 1,5-cyclooctadiene (COD) by nitrous oxide have been studied. The reaction proceeds without catalyst in the temperature range 473–553 K with the activation energy 113 kJ mol−1 and is first order with respect to the initial reactants. The mechanism includes consecutive ketonization of two C[DOUBLE BOND]C bonds in the COD molecule, with the intermediate formation of an unsaturated monoketone (MK). Further ketonization of MK leads to two isomeric diketones (DK): 1,4- and 1,5-cyclooctanedione. The 1,5-DK is a stable final product while the 1,4-DK undergoes further intramolecular aldol transformation leading to two bicyclic compounds, that retain the same number of carbon atoms. The distribution of mono- and diketones in the course of reaction is described by theoretical dependences pointing to identical reactivities of the C[DOUBLE BOND]C double bonds residing in COD and MK molecules. The ketonization of COD by nitrous oxide exemplifies a prospective way for the preparation of valuable organic products in perfect harmony with the strategy of green chemistry.
Библиографическая ссылка:
Ivanov D.P.
, Dubkov K.A.
, Babushkin D.E.
, Semikolenov S.V.
, Panov G.I.
Ketonization of 1,5-Cyclooctadiene by Nitrous Oxide
Advanced Synthesis and Catalysis. 2009. V.351. N11-12. P.1905-1911. DOI: 10.1002/adsc.200900278 WOS Scopus РИНЦ CAPlusCA OpenAlex
Ketonization of 1,5-Cyclooctadiene by Nitrous Oxide
Advanced Synthesis and Catalysis. 2009. V.351. N11-12. P.1905-1911. DOI: 10.1002/adsc.200900278 WOS Scopus РИНЦ CAPlusCA OpenAlex
Даты:
| Поступила в редакцию: | 20 апр. 2009 г. |
| Принята к публикации: | 8 июн. 2009 г. |
| Опубликована в печати: | 1 авг. 2009 г. |
| Опубликована online: | 13 авг. 2009 г. |
Идентификаторы БД:
| Web of science: | WOS:000269583900030 |
| Scopus: | 2-s2.0-68949163232 |
| РИНЦ: | 15309722 |
| Chemical Abstracts: | 2009:1012074 |
| Chemical Abstracts (print): | 152:429184 |
| OpenAlex: | W2035451341 |