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Concurrently with a study of the Oppenauer oxidation of dihydrocodeine1, we have been engaged in an investigation of the action of alkoxides upon certain derivatives of dihydromorphine. Because our results, though incomplete, are of value for preparative purposes and may also provide a means of clarifying a number of stereochemical problems in this field, we wish to report our findings to date.The stereochemical equilibration of an optically active alcohol has been most thoroughly investigated in the case of quinine (2). That alkaloid was converted by certain metallic alkoxides, excluding aluminum isopropoxide, to a mixture of four isomers: quinine, epf-quinine, quinidine, and ept-quinidine. By proper choice of experimental conditions it was possible to arrange this "partial raeemization" so as to obtain satisfactory yields of one of the isomers, e.g., quinidine.

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