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Abstract
The reaction in mixtures of adamantanone with hydroxylamine hydrochloride was studied in hydrochloric, hydrobromic, and hydroiodic acid solutions. In hydrochloric and hydroiodic acids, mixtures of isomers of 4-chloroadamantan-2-one and 4-iodoadamantan-2-one, respectively, are formed, whereas in hydrobromic acid in the presence of excess hydroxylamine hydrochloride, three stereoisomers of 4,8-dibromoadamantan-2-one appear. All the stereoisomeric haloketones were isolated by elution adsorption chromatography on silica gel or by crystalization. For the pure substances, their infrared, mass, and NMR spectra were measured.
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