Lead tetra-acetate oxidation of NN-dimethylglycine and its relevance to the biosynthesis of the pyrrolidine ring of nicotine

Abstract

A degradative sequence which has been used to determine the distribution of radioactivity in the pyrrolidine of nicotine involves, as one of the steps, the oxidation of NN-dimethylglycine with lead tetra-acetate; the formaldehyde produced in this reaction, formerly thought to originate entirely from C-2, has been shown to be derived in appreciable amounts from the N-methyl groups.