Microbiological hydroxylation of steroids. II. Structural information and infrared spectrometry: carbonyl, perturbed methylene, and hydroxy-vibrations of steroidal ketones and alcohols.

Abstract

High resolution i.r. spectrometry gives useful information about the structures of steroidal microbiological hydroxylation products. The polyketones formed by mild oxidation of the hydroxylation products are examined in the CO stretching and –CO–CH2– scissoring regions. Interpretation of the spectra by the characteristic group frequency approach is valid provided that the occurrence of interactions between carbonyl groups is recognised in predicting band positions and intensities. The hydroxylation products are most usefully studied, as dilute solutions, in the O–H stretching region. With compounds in which strong intramolecular hydrogen bonding occurs, the structures are almost uniquely defined by the characteristics of the O–H absorptions.