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alpha-organoelement nitrones: Synthesis, properties, and IR and C-13 NMR spectral and X-ray structural characterization Научная публикация

Журнал Organometallics
ISSN: 0276-7333
Вых. Данные Год: 2007, Том: 26, Номер: 7, Страницы: 1607-1615 Страниц : 9 DOI: 10.1021/om060883o
Авторы Voinov Maxim A. 2 , Shevelev Tikhon G. 3 , Rybalova Tatyana V. 1 , Gatilov Yury V. 1 , Pervukhina Natalie V. 3 , Burdukov Aleksei B. 3 , Grigor'ev Igor A. 1
Организации
1 Institute of Organic Chemistry, Avenue Akad. Lavrent'eva 9, 630090, Novosibirsk, Russia
2 Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204
3 Institute of Inorganic Chemistry, Avenue Akad. Lavrent'eva 5, 630090, Novosibirsk, Russia

Реферат: alpha-Organoelement-substituted nitrones have been synthesized for the first time through the reaction of the alpha-lithiated cyclic aldonitrones of 3-imidazoline 3-oxide, pyrroline 1-oxide, 2H-imidazole 1-oxide, and 3,4-dihydroisoquinoline 2-oxide series with electrophilic reagents such as HgCl2, (CH3)(3)SiCl, (C2H5)(3)GeCl, (n-C4H9)(3)SnBr, Ph2P(O)Cl, Ph2PCl, PhSSPh, PhSeSePh, TsCl, and TsF. Aldonitrones of the 3-imidazoline 3-oxide and pyrroline 1-oxide series were shown to readily afford the products of the lithiation-electrophilic substitution reaction. In contrast, aldonitrones of the 2H-imidazole 1-oxide and 3,4-dihydroisoquinoline 2-oxide series react smoothly only with halogen-free electrophiles. It was found that an aldonitrone group could be lithiated and selectively reacted with electrophiles even when kinetically more acidic methylene and amino groups are present in the molecule. Characteristic features of IR and C-13 NMR spectra of the compounds synthesized are discussed. Selected alpha-organoelement nitrones are characterized by an X-ray diffraction study.
Библиографическая ссылка: Voinov M.A. , Shevelev T.G. , Rybalova T.V. , Gatilov Y.V. , Pervukhina N.V. , Burdukov A.B. , Grigor'ev I.A.
alpha-organoelement nitrones: Synthesis, properties, and IR and C-13 NMR spectral and X-ray structural characterization
Organometallics. 2007. V.26. N7. P.1607-1615. DOI: 10.1021/om060883o WOS Scopus РИНЦ OpenAlex
Даты:
Опубликована online: 22 февр. 2007 г.
Опубликована в печати: 1 мар. 2007 г.
Идентификаторы БД:
Web of science: WOS:000244958600013
Scopus: 2-s2.0-34047253972
РИНЦ: 13546734
OpenAlex: W2088758232
Цитирование в БД:
БД Цитирований
Web of science 25
Scopus 27
РИНЦ 25
OpenAlex 23
Альметрики: