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Issue 17, 2014
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Regioisomeric allene dimer formation by the reaction of tetraarylbutatrienes with tetracyanoethene

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Abstract

The reaction of tetraarylbutatrienes (tetraaryl[3]cumulenes) with tetracyanoethene (TCNE), a strong electron-accepting molecule, at room temperature yielded novel four-membered ring compounds (head-to-tail unsymmetrically substituted diarylallene dimers) by [2 + 2] cycloaddition of the central C[double bond, length as m-dash]C bond of the butatrienes. This reaction proceeded through a head-to-head symmetrically substituted diarylallene dimer intermediate. Unsymmetrical butatriene also formed a small amount of another head-to-tail dimer. Although the allene dimer is stable in nonpolar solvents, it converts to other bicyclic and tricyclic compounds in MeOH or CH3CN at room temperature.

Graphical abstract: Regioisomeric allene dimer formation by the reaction of tetraarylbutatrienes with tetracyanoethene

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Publication details

The article was received on 24 Dec 2013, accepted on 25 Feb 2014 and first published on 26 Mar 2014


Article type: Paper
DOI: 10.1039/C3OB42574F
Citation: Org. Biomol. Chem., 2014,12, 2784-2791
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    Regioisomeric allene dimer formation by the reaction of tetraarylbutatrienes with tetracyanoethene

    S. Ueta, K. Hida, M. Nishiuchi and Y. Kawamura, Org. Biomol. Chem., 2014, 12, 2784
    DOI: 10.1039/C3OB42574F

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