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Facile insertion of ethylene into a group 14 element-carbon bond: effects of the HOMO–LUMO energy gap on reactivity

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Abstract

The diarylstannylenes, Sn(AriPr4)2 and Sn(AriPr6)2, (AriPr4 = C6H3-2,6-(C6H3-2,6-iPr2)2, AriPr6 = C6H3-2,6-(C6H2-2,4,6-iPr3)2), undergo a facile migratory insertion reaction with ethylene at 60 °C to afford the alkyl aryl stannylenes AriPr4SnCH2CH2AriPr4 and AriPr6SnCH2CH2AriPr6 which were characterized via 1H, 13C and 119Sn NMR, UV-vis and IR spectroscopy, as well as by X-ray crystallography. Quantum mechanical calculations were performed, and two potential mechanisms were identified, with a migratory insertion reaction pathyway being energetically preferred.

Graphical abstract: Facile insertion of ethylene into a group 14 element-carbon bond: effects of the HOMO–LUMO energy gap on reactivity

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Publication details

The article was received on 24 Oct 2018, accepted on 28 Nov 2018 and first published on 05 Dec 2018


Article type: Communication
DOI: 10.1039/C8CC08488B
Citation: Chem. Commun., 2019, Advance Article
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    Facile insertion of ethylene into a group 14 element-carbon bond: effects of the HOMO–LUMO energy gap on reactivity

    T. Y. Lai, J. Guo, J. C. Fettinger, S. Nagase and P. P. Power, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C8CC08488B

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