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Preparation of Heptafluoronaphthyllithiums and -Magnesiums: An Unexpected Difference in the Reactivity of Isomers C10F7H and C10F7Br Towards Organolithium and Organomagnesium Compounds Научная публикация

Журнал Journal of Organometallic Chemistry
ISSN: 0022-328X
Вых. Данные Год: 2019, Том: 899, Номер статьи : 120889, Страниц : 10 DOI: 10.1016/j.jorganchem.2019.120889
Ключевые слова Alkyllithium; Bromoheptafluoronaphthalene; Ethylmagnesium bromide; Heptafluoronaphthalene; Metalation; Trimethylsilylheptafluoronaphthalene
Авторы Shmakov Mikhail M. 1,2 , Bardin Vadim V. 2,3 , Prikhod'ko Sergey A. 1,2 , Adonin Nicolay Yu. 1,2
Организации
1 Boreskov Institute of Catalysis, SB RAS, Acad. Lavrentiev Ave. 5, Novosibirsk, 630090, Russian Federation
2 Novosibirsk State University, Pirogova Str. 2, Novosibirsk, 630090, Russian Federation
3 Vorozhtsov Novosibirsk Institute of Organic Chemistry, SB RAS, Acad. Lavrentiev Ave. 9, Novosibirsk, 630090, Russian Federation

Информация о финансировании (2)

1 Российский фонд фундаментальных исследований 16-29-10762
2 Министерство науки и высшего образования Российской Федерации (с 15 мая 2018) ГЗ-2017-2020

Реферат: Significant differences in the reactivity of isomeric heptafluoronaphthalenes and bromoheptafluoronaphthalenes towards organolithium and organomagnesium compounds were found. Metalation of polyfluorinated naphthalenes 2-C10F7X (X = H, Br) occurs easily under the action of bases (BuLi, t-BuLi, LDA) as well as EtMgBr (X = Br) in ether. This fact was proven by 19F NMR spectroscopy and by trapping of 2-C10F7M (M = Li, MgBr, Mg(2-C10F7)) with electrophile ClSiMe3. The interaction of 1-C10F7Br with BuLi or EtMgBr proceeds in a similar way. In contrast to 2-C10F7H, isomeric 1-C10F7H is the less acidic substrate and undergoes only the nucleophilic alkyldefluorination when combined with BuLi or t-BuLi. © 2019
Библиографическая ссылка: Shmakov M.M. , Bardin V.V. , Prikhod'ko S.A. , Adonin N.Y.
Preparation of Heptafluoronaphthyllithiums and -Magnesiums: An Unexpected Difference in the Reactivity of Isomers C10F7H and C10F7Br Towards Organolithium and Organomagnesium Compounds
Journal of Organometallic Chemistry. 2019. V.899. 120889 :1-10. DOI: 10.1016/j.jorganchem.2019.120889 WOS Scopus РИНЦ CAPlus OpenAlex
Даты:
Поступила в редакцию: 27 февр. 2019 г.
Принята к публикации: 8 авг. 2019 г.
Опубликована online: 11 авг. 2019 г.
Опубликована в печати: 30 окт. 2019 г.
Идентификаторы БД:
Web of science: WOS:000485104600018
Scopus: 2-s2.0-85070596364
РИНЦ: 41626595
Chemical Abstracts: 2019:1621285
OpenAlex: W2967366388
Цитирование в БД: Пока нет цитирований
Альметрики: