Configurations of the 5-methyladamantan-2-ols and the 2,5-dimethyl-adamantan-2-ols

Abstract

The configurations of the two secondary and the two tertiary alcohols whose synthesis is described in the preceding paper have been established unambiguously by analysis of n.m.r. spectra. Four techniques were used : (i) treatment of chemical shifts by the additivity relationship; (ii) study of degree to fit to the relationship between europium-induced shift and intramolecular distance; (iii) comparison between sensitivities of shifts to europium concentration; and (iv) investigation of the behaviour of the previously assigned protons of adamantan-2-ol, and spin decoupling in the europium-expanded spectrum. All results led to the same conclusions, and justify interchange of the configurations previously assigned to the secondary alcohols. The reliability of these methods is assessed.