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Issue 9, 2017
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A mechanistic study on cationic Li prompted Diels–Alder cycloaddition of cycloparaphenylene

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Abstract

We introduce Li+ involving cycloadditions between acetylene and ring-like cycloparaphenylenes (CPPs) in theory. Orbital analysis suggests an inverse electron-demand mechanism in which the diene CPP acts as an electron acceptor. Partial electron transfer to Li+ results in a reduced and localized π* orbital of CPP, giving rise to a site-selective reaction with a much smaller barrier.

Graphical abstract: A mechanistic study on cationic Li prompted Diels–Alder cycloaddition of cycloparaphenylene

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Publication details

The article was received on 14 Apr 2017, accepted on 01 Jun 2017 and first published on 02 Jun 2017


Article type: Research Article
DOI: 10.1039/C7QO00290D
Citation: Org. Chem. Front., 2017,4, 1757-1761
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    A mechanistic study on cationic Li prompted Diels–Alder cycloaddition of cycloparaphenylene

    J. Dang, W. Wang, X. Zhao and S. Nagase, Org. Chem. Front., 2017, 4, 1757
    DOI: 10.1039/C7QO00290D

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