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1-Oxo-1H-phenalene-2,3-dicarbonitrile heteroaromatic scaffold: revised structure and mechanistic studies

Romaric Lenk1, Arnaud Tessier, Pierre Lefranc

  • 1Université de Nantes, CNRS, CEISAM, UMR CNRS 6230 , Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France.

The Journal of Organic Chemistry
|September 27, 2014
PubMed

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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