A Metallaanthracene and Derived Metallaanthraquinone. (20th October 2016)

• Record Type: Journal Article
• Authors: Frogley, Benjamin J.; Wright, L. James
• Is Part Of: Angewandte Chemie. Volume 129:Number 1(2017)
• Page Start: 149
• Page End: 153
• Publication Date: 2016-10-20
• Subjects: Cyclisierungen -- Iridium -- Kondensierte Metallabenzole -- Metallaanthracen -- Metallacyclen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201608500
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Metalla‐analogues of archetypal aromatic molecules are attracting ever increasing interest. Although metallabenzenes (which fall within this class) have been well studied, fused‐ring metallabenzenes are rare and of the linear polycyclic metallaaromatic hydrocarbons, only metallanaphthalene is known. Herein we report the first metallaanthracene, [Ir(C13 H8 {CH2 CO2 Me‐5})Cl(PPh3 )2 ]O3 SCF3 (5 ), which represents the next member of this series of polycyclic compounds. Structurally, 5 has a number of features in common with anthracene including fused‐ring planarity and bond‐length alternation. In analogues of classic reactions of anthracene, 5 forms a Diels–Alder adduct with maleic anhydride and on oxidation the unprecedented fused‐ring metallaanthraquinone, [Ir(C15 H6 O{Br‐6}{OMe‐7}{=O‐8}{=O‐15})Br(PPh3 )2 ], is obtained. Abstract : Das Spektrum der Metalla‐Analoga linearer polycyclischer aromatischer Kohlenwasserstoffe wurde durch die gezielte Synthese eines Iridaanthracens auf Metallaanthracene ausgedehnt. In Anlehnung an klassische Anthracen‐Reaktionen bildet das Iridaanthracen ein Diels‐Alder‐Addukt mit Maleinsäureanhydrid, und seine Oxidation liefert ein kondensiertes Metallaanthrachinon.