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Dual reactivity of secondary phosphines and their chalcogenides towards 1-(vinyloxy)alkylferrocenes: the switch between alpha- and beta-addition Научная публикация

Журнал Tetrahedron
ISSN: 0040-4020
Вых. Данные Год: 2015, Том: 71, Номер: 13, Страницы: 1998-2003 Страниц : DOI: 10.1016/j.tet.2015.02.011
Ключевые слова Addition; Enol ethers; Ferrocene; Regioselectivity; Phosphines
Авторы Artem'ev Alexander V. 1 , Oparina Ludmila A. 1 , Gusarova Nina K. 1 , Vysotskaya Oksana V. 1 , Tarasova Olga A. 1 , Gatilov Yuriy V. 2,3 , Albanov Alexander I. 1 , Trofimov Boris A. 1
Организации
1 (Данные Web of science) Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, Irkutsk 664033, Russia
2 (Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
3 (Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

Реферат: The secondary phosphines and their sulfides regioselectively add, under free radical conditions (AIBN, 65 degrees C or UV-irradiation, rt), to (vinyloxy)methyl- and 1-(vinyloxy)ethylferrocenes to give anti-Markov-nikov adducts in high yields. Without any initiator, the secondary phosphine selenides, when reacted with the above alkenes (rt, 24 h), selectively form Markovnikov adducts, which readily decompose upon handling to afford diorganyl[1-(ferrocenyl)alkyl]phosphine selenides, R2P(Se)CH(R')Fc (R=Ph; R'=H or Me) in 28-39% isolated yields. The synthesized compounds were characterized using H-1, C-13, P-31 NMR, and FTIR spectroscopy as well as X-ray diffraction analysis. (C) 2015 Elsevier Ltd. All rights reserved.
Библиографическая ссылка: Artem'ev A.V. , Oparina L.A. , Gusarova N.K. , Vysotskaya O.V. , Tarasova O.A. , Gatilov Y.V. , Albanov A.I. , Trofimov B.A.
Dual reactivity of secondary phosphines and their chalcogenides towards 1-(vinyloxy)alkylferrocenes: the switch between alpha- and beta-addition
Tetrahedron. 2015. V.71. N13. P.1998-2003. DOI: 10.1016/j.tet.2015.02.011 WOS Scopus РИНЦ OpenAlex
Даты:
Опубликована в печати: 1 апр. 2015 г.
Идентификаторы БД:
Web of science: WOS:000352747900014
Scopus: 2-s2.0-84923861185
РИНЦ: 24010973
OpenAlex: W2052082326
Цитирование в БД:
БД Цитирований
Web of science 7
Scopus 6
РИНЦ 6
OpenAlex 6
Альметрики: