Nitrones and Oxaziridines. XXXVIII. Nitric Acid Oxidation of Some Pyrroline 1-Oxides

Abstract

2,4-Diaryl-5,5-dimethyl-1-pyrroline 1-oxides (5)-(7) undergo smooth oxidation by concentrated nitric acid in acetonitrile to give the hydroxy ketones (9)-(11). Reduction of compound (10) with sodium borohydride gives the diol (22), which can be dehydrated to the oxo nitrone (23). The stereochemical assignments of the alcohol (8) and the diol (22) are discussed.