HOMOLYTIC OXOALKYLATION OF PROTONATED N-HETEROAROMATIC COMPOUNDS

The oxoalkylation of pyridine, 2-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-pyridines, quinoline, 4-methylquinoline, isoquinoline, and pyrazine with oxoalkyl radicals generated from 1-methylcyclobutanol or 1-methylcyclopentanol under the action of Pb(OAc)4 or Mn(OAc)3 has been carried out. The reaction products are isomers with 2-(6)- and 4-positions of the oxoalkyl group in the N-heteroaromatic ring. The isomer ratios have been determined as a function of the structure of the N-heteroaromatic compound and the reaction conditions.