Dual reactivity of secondary phosphines and their chalcogenides towards 1-(vinyloxy)alkylferrocenes: the switch between alpha- and beta-addition Full article
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Tetrahedron
ISSN: 0040-4020 |
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| Output data | Year: 2015, Volume: 71, Number: 13, Pages: 1998-2003 Pages count : DOI: 10.1016/j.tet.2015.02.011 | ||||||
| Tags | Addition; Enol ethers; Ferrocene; Regioselectivity; Phosphines | ||||||
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Abstract:
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.
Cite:
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
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
Dates:
| Published print: | Apr 1, 2015 |
Identifiers:
| Web of science: | WOS:000352747900014 |
| Scopus: | 2-s2.0-84923861185 |
| Elibrary: | 24010973 |
| OpenAlex: | W2052082326 |