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Synthesis 2000; 2000(10): 1469-1473
DOI: 10.1055/s-2000-7118
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An Unusual Route for the Regioselective Acylation of Polycyclic Aromatic Hydrocarbons: Nitrile Oxide Addition Followed by Isoxazoline Degradation

Antonino Corsaro* , Ugo Chiacchio, Vito Librando, Venerando Pistarà, Antonio Rescifina
  • *Dipartimento di Scienze Chimiche, Università di Catania, viale A Doria 6, I-95125 Catania, Italy; Fax + 39(95)58 01 38; E-mail: acorsaro@dipchi.unict.it
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Publication Date:
31 December 2000 (online)

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By treatment with a base such as sodium methoxide or surprisingly lithium aluminium hydride monocycloadducts 1a - c afforded the corresponding oximes 2a - c which were oxidized to ketones 3a - c by the Dess-Martin method. The same ketones 3a - c are obtained by reductive ring opening of 1a - c with Raney-Ni. Monocycloadducts 1d - h also have oximes 2d - h upon treatment with the same bases, but complex reaction mixtures were obtained when oximes 2d - h were subjected to oxidation or monocycloadducts 1d - h were subjected to reduction with Raney-Ni.

polycyclic aromatic hydrocarbons - hydrogenations - ketones - oximes - oxidations - ring opening

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