Hydroxy-steroids. Part XI. The preparation and infrared spectra of vicinal cholestanediols

Abstract

Twenty-eight vicinal cholestanediols (positions 1,2; 2,3; 3,4; 4,5; 5,6; 6,7; and 7,8) have been prepared by unambiguous routes starting from the corresponding olefins. The O–H stretching bands of dilute solutions of these diols and of seven reference compounds have been examined under high dispersion. Characteristic differences between ax,ax, ax,eq, and eq,eq compounds were observed. It was concluded that precise values for the dihedral angles between the hydroxy-groups cannot be obtained from the frequency difference between the absorptions of the free and bonded hydroxy-groups.