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Updated: Oct 3, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Cycloaddition of isoselenocyanates to sodium and magnesium metallacycles
Vladimir A Dodonov1, Olga A Kushnerova1, Roman V Rumyantsev1
1G.A. Razuvaev Institute of Organometallic Chemistry of the Russian Academy of Sciences. Tropinina str. 49, N. Novgorod 603137, Russia. igorfed@iomc.ras.ru.
Abstract:
Heterocumulenes SeCNR (R = C6H4OMe-2, C6H4Me-2) undergo facile cycloaddition to [(H-dpp-bian)Na(Et2O)2] (1) (H-dpp-bian = N-protonated 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene) resulting in cycloadducts [(H-dpp-bian)Na(SeCNR)(DME)] (2, 3), which are the first cycloadducts derived from a sodium metallacycle reported so far. A comparative reaction of [(dpp-bian)Mg(THF)3] (10) with SeCNR gives magnesium cycloadducts [(dpp-bian)Mg(SeCNR)(Solv)2] (11, 12), which undergo fast decomposition at room temperature. New compounds are characterized by NMR, EPR, and IR spectroscopy, and elemental and X-ray diffraction analysis. Their electronic structures and reaction pathways were probed using DFT calculations.
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