Oxidation of Cycloalkenes and Methylenecycloalkanes by Palladium(II) Complexes. Part 2. NMR Study on the Mechanism of the Ring Expansion of Methylenecyclobutane Научная публикация
Журнал |
Journal of Molecular Catalysis (Continued after 1994 as Journal of Molecular Catalysis A: Chemical and Journal of Molecular Catalysis B: Enzymatic)
ISSN: 0304-5102 |
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Вых. Данные | Год: 1993, Том: 83, Номер: 3, Страницы: 301-310 Страниц : 10 DOI: 10.1016/0304-5102(93)87040-F | ||
Ключевые слова | cycloalkene oxidation, methylenecyclobutane, oxidation, palladium | ||
Авторы |
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Организации |
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Реферат:
The reaction of methylenecyclobutane (1) with bis(acetonitrile)chloronitropalladium(II) in methylene chloride yields cyclopentanone. Two intermediates - π-olefin complex of palladium and product of β-nitritopalladation of 1 in a Markovnikov fashion - are observed by 1H and 13C NMR. Palladium-catalyzed ring expansion of 1 is suggested to involve heterolysis of the palladium-carbon bond and rearrangement of the resulting cyclobutyl to cyclopentyl cations. The selective formation of ring-expanded and ring-contracted carbonyl products from methylenecyclobutane and
1-methyleyclobutene, respectively, is discussed in terms of proposed mechanism.
Библиографическая ссылка:
Beck I.E.
, Gusevskaya E.V.
, Golovin A.V.
, Likholobov V.A.
Oxidation of Cycloalkenes and Methylenecycloalkanes by Palladium(II) Complexes. Part 2. NMR Study on the Mechanism of the Ring Expansion of Methylenecyclobutane
Journal of Molecular Catalysis (Continued after 1994 as Journal of Molecular Catalysis A: Chemical and Journal of Molecular Catalysis B: Enzymatic). 1993. V.83. N3. P.301-310. DOI: 10.1016/0304-5102(93)87040-F WOS Scopus РИНЦ
Oxidation of Cycloalkenes and Methylenecycloalkanes by Palladium(II) Complexes. Part 2. NMR Study on the Mechanism of the Ring Expansion of Methylenecyclobutane
Journal of Molecular Catalysis (Continued after 1994 as Journal of Molecular Catalysis A: Chemical and Journal of Molecular Catalysis B: Enzymatic). 1993. V.83. N3. P.301-310. DOI: 10.1016/0304-5102(93)87040-F WOS Scopus РИНЦ
Даты:
Поступила в редакцию: | 10 сент. 1992 г. |
Принята к публикации: | 20 мар. 1993 г. |
Опубликована в печати: | 30 июл. 1993 г. |
Опубликована online: | 2 окт. 2001 г. |
Идентификаторы БД:
Web of science | WOS:A1993LQ32700004 |
Scopus | 2-s2.0-0027626237 |
РИНЦ | 31642004 |
Chemical Abstracts | 1994:30336 |
Chemical Abstracts (print) | 120:30336 |
OpenAlex | W2038348310 |