title: 1-Oxo-1H-phenalene-2,3-dicarbonitrile heteroaromatic scaffold: revised structure and mechanistic studies.
abstract: 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.
authors.affiliation: 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.
authors.forename: Romaric
authors.initials: R
authors.lastname: Lenk
authors.forename: Arnaud
authors.initials: A
authors.lastname: Tessier
authors.forename: Pierre
authors.initials: P
authors.lastname: Lefranc
authors.forename: Virginie
authors.initials: V
authors.lastname: Silvestre
authors.forename: Aurélien
authors.initials: A
authors.lastname: Planchat
authors.forename: Virginie
authors.initials: V
authors.lastname: Blot
authors.forename: Didier
authors.initials: D
authors.lastname: Dubreuil
authors.forename: Jacques
authors.initials: J
authors.lastname: Lebreton
mesh_terms: D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D014961:X-Ray Diffraction
chemical_list: C000597412:1-oxo-1H-phenalene-2,3-dicarbonitrile; C000597413:8-oxo-8H-acenaphtho(1,2-b)pyrrol-9-carbonitrile; D006571:Heterocyclic Compounds; D009570:Nitriles; D011758:Pyrroles