Abstract
The reduction of quaternary 1-(adamantan-1-yl)pyridinium salts with sodium borohydride in ethanol gave 1-(adamantan-1-yl)-1,2,3,6-tetrahydropyridines that reacted with benzene in trifluoromethanesulfonic acid medium, leading to the formation of 1-(adamantan-1-yl)-phenylpiperidines with various spatial orientation of the phenyl substituent. The structure of the obtained phenylpiperidines was confirmed by the spectral dataset. The thermodynamic stability calculations for the conformers of phenylpiperidines were performed with the B3LYP/6-311++(d,p) method.
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