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Issue 83, 2017
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An exploding N-isocyanide reagent formally composed of anthracene, dinitrogen and a carbon atom

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Abstract

Targeted as an example of a compound composed of a carbon atom together with two stable neutral leaving groups, 7-isocyano-7-azadibenzonorbornadiene, CN2A (1, A = C14H10 or anthracene) has been synthesized and spectroscopically and structurally characterized. The terminal C atom of 1 can be transferred: mesityl nitrile oxide reacts with 1 to produce carbon monoxide, likely via intermediacy of the N-isocyanate OCN2A. Reaction of 1 with [RuCl2(CO)(PCy3)2] leads to [RuCl2(CO)(1)(PCy3)2] which decomposes unselectively: in the product mixture, the carbide complex [RuCl2(C)(PCy3)2] was detected. Upon heating in the solid state or in solution, 1 decomposes to A, N2 and cyanogen (C2N2) as substantiated using molecular beam mass spectrometry, IR and NMR spectroscopy techniques.

Graphical abstract: An exploding N-isocyanide reagent formally composed of anthracene, dinitrogen and a carbon atom

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The article was received on 18 Aug 2017, accepted on 26 Sep 2017 and first published on 26 Sep 2017


Article type: Communication
DOI: 10.1039/C7CC06516G
Citation: Chem. Commun., 2017,53, 11500-11503
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    An exploding N-isocyanide reagent formally composed of anthracene, dinitrogen and a carbon atom

    M. Joost, M. Nava, W. J. Transue and C. C. Cummins, Chem. Commun., 2017, 53, 11500
    DOI: 10.1039/C7CC06516G

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