Studies on the reaction of benzoyl peroxide with NN-disubstituted aromatic amines and related compounds. Part VI. Some attempts to effect o-hydroxylation in the strychnine series

Abstract

Attempts to protect the carboxy-group of strychnic acid so as to allow hydroxylation in the 4-position by means of dibenzoyl peroxide were unsuccessful. The Wieland–Gumlich aldehyde methyl ether (5) and its 12-epimer reacted with dibenzoyl peroxide to yield the corresponding N_b-oxides. 11-lsonitroso-N-methyl-sec-pseudostrychnine was prepared, but we were unable to convert it into a compound analogous to the Wieland–Gumlich aldehyde.