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

J Org Chem

Université 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.

Published: October 2014

Synthesis of the originally proposed 8-oxo-8H-acenaphtho[1,2-b]pyrrol-9-carbonitrile led to a structural revision, and the product has now been identified as unknown compound 1-oxo-1H-phenalene-2,3-dicarbonitrile. The structural assignment was corroborated by detailed NMR studies and unambiguously confirmed by X-ray diffraction. A mechanism is proposed to explain the formation of this original heterocyclic scaffold. In addition, some new chemical transformations involving this compound are presented.

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http://dx.doi.org/10.1021/jo5016932DOI Listing

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