Attempts to prepare aromatic O-acyl-hydroxylamines—I : Dehydrohalogenation of 1-bromo-4-acetoxyimino-1,2,3,4-tetrahydrophenanthrene by tetramethylammonium dimethylphosphate

The dehydrohalogenation of 1-bromo-4-acetoxyimino-1,2,3,4-tetrahydrophenanthrene by tetramethylammonium dimethylphosphate gave a mixture of products. Ten of these were identified and together account for 70% of the total yield. The proposed reaction mechanism implicates the corresponding O-acetyl-hydroxylamine 15 as an intermediate. Attempts to prepare O-esters or O-ethers of aromatic hydroxylamines by dehydrogenation, with quinones, of the corresponding oximino-derivatives of oxo-1,2,3,4-tetrahydro-naphthalene and oxo-1,2,3,4-tetrahydro-phenanthrene were without success.