A. Corsaro et al., An unusual route for the regioselective acylation of polycyclic aromatic hydrocarbons: Nitrile oxide addition followed by isoxazoline degradation, SYNTHESIS-S, (10), 2000, pp. 1469-1473
By treatment with a base such as sodium methoxide or surprisingly lithium a
luminium 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 gave oximes 2d-h upon treatment with the same ba
ses, but complex reaction mixtures were obtained when oximes 2d-h were subj
ected to oxidation or monocycloadducts 1d-h were subjected to reduction wit
h Raney-Ni.