An unusual route for the regioselective acylation of polycyclic aromatic hydrocarbons: Nitrile oxide addition followed by isoxazoline degradation
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 r