The reaction of pyridine 1‐oxide with 1‐adamantanethiol in acetic anhydride produced a mixture of 2‐ and 3‐(1‐adamantanethio)pyridines, 1‐aeetyl‐2‐(1‐adamantanethio)‐3‐hydroxy‐4‐acetoxy‐1,2,3,4‐telrahydropyridine and the corresponding 3‐acetoxyderivative. Pure substances were separated by means of column chromatography on alumina. The tetrahydropyridines were identified by means of their proton magnetic and mass spectra. 4‐(1‐Adamantanethio)pyridine was synthesized from 4‐chloropyridinc and 1‐adamantanethiol. The three isomeric (1‐adamantanethio)‐pyridines were, each, cleaved by concentrated hydrochloric acid to give 1‐chloroadamantane and the corresponding pyridinethiol.
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Mikrut et al. (1974) studied this question.
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