Dual reactivity of secondary phosphines and their chalcogenides towards 1-(vinyloxy)alkylferrocenes: the switch between α- and β-addition
2015
Artem'ev, Alexander V. | Oparina, Ludmila A. | Gusarova, Nina K. | Vysotskaya, Oksana V. | Tarasova, Olga A. | Gatilov, Yuriy V. | Albanov, Alexander I. | Trofimov, Boris A.
The secondary phosphines and their sulfides regioselectively add, under free radical conditions (AIBN, 65 °C or UV-irradiation, rt), to (vinyloxy)methyl- and 1-(vinyloxy)ethylferrocenes to give anti-Markovnikov 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 1H, 13C, 31P NMR, and FTIR spectroscopy as well as X-ray diffraction analysis.
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