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
|
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.