1‑Oxo‑1H‑phenalene-2,3-dicarbonitrile Heteroaromatic Scaffold: Revised Structure and Mechanistic Studies

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 c...

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Veröffentlicht in:	Journal of organic chemistry 2014-10, Vol.79 (20), p.9754-9761
Hauptverfasser:	Lenk, Romaric, Tessier, Arnaud, Lefranc, Pierre, Silvestre, Virginie, Planchat, Aurélien, Blot, Virginie, Dubreuil, Didier, Lebreton, Jacques
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemical Sciences Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Magnetic Resonance Spectroscopy Molecular Structure Nitriles - chemical synthesis Nitriles - chemistry Pyrroles - chemical synthesis Pyrroles - chemistry X-Ray Diffraction
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container_end_page	9761
container_issue	20
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container_title	Journal of organic chemistry
container_volume	79
creator	Lenk, Romaric Tessier, Arnaud Lefranc, Pierre Silvestre, Virginie Planchat, Aurélien Blot, Virginie Dubreuil, Didier Lebreton, Jacques
description	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.
doi_str_mv	10.1021/jo5016932
format	Article
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subjects	Chemical Sciences Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Magnetic Resonance Spectroscopy Molecular Structure Nitriles - chemical synthesis Nitriles - chemistry Pyrroles - chemical synthesis Pyrroles - chemistry X-Ray Diffraction
title	1‑Oxo‑1H‑phenalene-2,3-dicarbonitrile Heteroaromatic Scaffold: Revised Structure and Mechanistic Studies
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