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Issue 71, 2014
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Oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′-diamines (BINAMs) via C–C bond cleavage and nitrogen migration: a versatile synthesis of U-shaped azaacenes

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Abstract

An oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′-diamines (BINAMs) that involves the cleavage of a strong C–C single bond of the binaphthalene unit and the nitrogen migration has been discovered. The unprecedented rearrangement enables access to a series of U-shaped azaacenes otherwise difficult to prepare in a selective manner by classical methods. Moreover, physicochemical properties of the unique azaacenes have been comprehensively investigated.

Graphical abstract: Oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′-diamines (BINAMs) via C–C bond cleavage and nitrogen migration: a versatile synthesis of U-shaped azaacenes

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Publication details

The article was received on 27 Jun 2014, accepted on 13 Jul 2014 and first published on 17 Jul 2014


Article type: Communication
DOI: 10.1039/C4CC04911J
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Citation: Chem. Commun., 2014,50, 10291-10294
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    Oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′-diamines (BINAMs) via C–C bond cleavage and nitrogen migration: a versatile synthesis of U-shaped azaacenes

    Y. Takeda, M. Okazaki and S. Minakata, Chem. Commun., 2014, 50, 10291
    DOI: 10.1039/C4CC04911J

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