Robert F. Francis

THE CATALYTIC ALPHA-METHYLATION OF PYRIDINES

compound. The major products of this reaction, 2-ethylpyridine and 2-ethyl-6methylpyridine, could be envisioned as arising not by hydrogenation but by dehydroxymethylation and dehydroxymethylation plus a-methylation, respectively. Because of the unusual nature of these reactions, as well as their potential synthetic utility, a more detailed investigation was undertaken. Although the a-methylation reaction appears to be without precedent in the literature, the dehydroxymethylation of primary alcohols has been investigated under two basically different sets of experimental conditions. Ipatieff and Pines found that a variety of primary alcohols are dehydroxymethylated in the presence of a nickel catalyst, with 3-5 or withouts added hydrogen, to produce the alkane containing one less carbon atom, methane, and water (reaction 3) . Under reductive desulfuration conditions, however, Bonner, et al. observed that dehy-

General synthesis of 2,6-dialkylpyridines

The reactions of pyridine with excess of alkyl-lithium compounds generally give excellent yields of 2,6-dialkylpyridines.