Transformations with Alcohols and Phenols

In the presence of sodium borohydride in methanol, epoxycholestanes are opened regioselectively (Eq. 304).  

The reaction seen in Eq. 305 results in oxetane derivatives by means of neighboring-group participation (Eq. 305).  

The role of steric factors has been examined in the opening of polyfluorinated oxiranes. Accounts have been given of the alcoholysis of steroid oxiranes and their transformation with phenol.The kinetics of the reactions of oxiranes with alcohols and phenols have been reported in a number of publications. The catalytic influence of transition metals has been examined. A secondary deuterium isotope effect has been studied in the course of methanolysis, and the solvent effect has been considered in reactions with phenols.  

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