Separation and Identification of Bridgehead-Substituted Methyl and Ethyl Adamantanes

Abstract

A combination of gas chromatography, infrared and nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry was used to characterize the products obtained from aluminum halide-catalyzed isomerizations of tricyclic saturated hydrocarbons. Six compounds were isolated and identified as methyl and ethyl bridgehead-substituted adamantane derivatives. In addition to supplying evidence pertinent to the structural proof of these derivatives, the data provide useful correlations between infrared, NMR, and mass spectra and methyl and ethyl bridgehead substitution of the adamantane nucleus. A complex splitting pattern which was observed in the NMR spectra of the ethyl-substituted derivatives was shown to be due to the unique A₂B₃ splitting of the bridgehead-ethyl group.

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