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1,3-Diaza[3]ferrocenophanes Functionalized with a Nitronyl Nitroxide Group Научная публикация

Общая информация Язык: Английский, Жанр: Статья (Full article),
Статус опубликования: Опубликована, Оригинальность: Оригинальная
Журнал Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416
Вых. Данные Год: 2018, Том: 74, Номер: 15, Страницы: 1942-1950 Страниц : 9 DOI: 10.1016/j.tet.2018.02.062
Ключевые слова Iminophosphoranes, Arylisocyanates, aza-Wittig reaction, Phosphonium betaines, 1,3-Diaza[3]ferrocenophane, Nitronyl nitroxides, Monocrystal XRD
Авторы Gurskaya Larisa 1 , Bagryanskaya Irina 1,2 , Amosov Evgeny 1 , Kazantsev Maxim 1,2 , Politanskaya Larisa 1 , Zaytseva Elena 1 , Bagryanskaya Elena 1,2 , Chernonosov Aleksander 3 , Tretyakov Evgeny 1,2
Организации
1 N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Ac. Lavrentiev Avenue, Novosibirsk 630090, Russia
2 National Research University - Novosibirsk State University, Novosibirsk 630090, Russia
3 Institute of Chemical Biology & Fundamental Medicine, 8 Ac. Lavrentiev Avenue, Novosibirsk 630090, Russia

Информация о финансировании (2)

1 Министерство образования и науки Российской Федерации Проект 5-100
2 Российский фонд фундаментальных исследований 15-03-01850

Реферат: An aza-Wittig reaction of 1,10-bis(triphenylphosphoranylidenamino)-ferrocene with 4-iodo-, 2,5-difluoro-4-iodo-, pentafluoro-, or 4-methoxycarbonylphenylisocyanates is described here. Intermediate betaines, which are products of a nucleophilic attack of the nitrogen atom of the remaining iminophosphorane moiety on the carbon atom of the carbodiimide functional group, were isolated; their structures were proved by monocrystal X-ray diffraction. Hydrolysis of the betaines under mild conditions gave corresponding arylamino-1,3-diaza[3]ferrocenophanes. On the other hand, as demonstrated, under more rigid conditions, the betaines could be converted into ferrocenophanes with the 1,3- diazetidine-2,4-diimine coupler. The iodo- or diiodo-derivatives of 1,3-diaza[3]ferrocenophanes were cross-coupled with a nitronyl nitroxide-2-ide gold(I) complex to obtain corresponding metallocenophanes functionalized with the nitronyl nitroxide group(s). The molecular and crystal structures of the halogenated and spin-labeled ferrocenophanes were solved by X-ray analysis. In arylamino-1,3-diaza [3]ferrocenophanes, according to cyclic voltammetry, the position of the quasi-reversible oxidation peak associated with the Fe(II)/Fe(III) redox couple deviates within 0.09 V depending on substituents in the arylamino group.
Библиографическая ссылка: Gurskaya L. , Bagryanskaya I. , Amosov E. , Kazantsev M. , Politanskaya L. , Zaytseva E. , Bagryanskaya E. , Chernonosov A. , Tretyakov E.
1,3-Diaza[3]ferrocenophanes Functionalized with a Nitronyl Nitroxide Group
Tetrahedron. 2018. V.74. N15. P.1942-1950. DOI: 10.1016/j.tet.2018.02.062 WOS Scopus РИНЦ
Даты:
Поступила в редакцию: 9 янв. 2018 г.
Принята к публикации: 26 февр. 2018 г.
Опубликована online: 8 мар. 2018 г.
Опубликована в печати: 1 апр. 2018 г.
Идентификаторы:
Web of science WOS:000430028400025
Scopus 2-s2.0-85042936657
РИНЦ 35507548
Chemical Abstracts 2018:417509
Chemical Abstracts (print) 168:337750
Альметрики: