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Facile Insertion of Ethylene into a Group 14 Element-Carbon Bond: Effects of the HOMO-LUMO Energy Gap on Reactivity

Abstract

Facile Insertion of Ethylene into a Group 14 Element-Carbon Bond: Effects of the HOMO-LUMO Energy Gap on Reactivity Ting Yi Lai,a Jing-Dong Guo, b,c James C. Fettinger,a Shigeru Nagaseb,c and Philip P. Power a* The diarylstannylenes, Sn(AriPr4)2 and Sn(AriPr6)2, (AriPr4 = C6H3-2,6-(C6H3-2,6-iPr 2)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 pathway being energetically preferred.

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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., 2018, Accepted Manuscript
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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. D. Guo, J. C. Fettinger, S. Nagase and P. P. Power, Chem. Commun., 2018, Accepted Manuscript , DOI: 10.1039/C8CC08488B

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