Arylation of Aromatic compounds. VI. Benzoyl Peroxide with Pyridine and Quinoline

Abstract

Amongst the products formed when pyridine reacts with benzoyl peroxide are phenylpyridines, benzoic acid, pyridine oxide, and dipyridyls. The molar yield of benzoic acid is significantly higher than that of the phenylpyridines although most aromatic compounds give approximately equal yields of benzoic acid and phenylated compounds. This difference may be ascribed to the simultaneous formation of pyridine oxide and dipyridyls. Similar remarks apply to the reaction with quinoline and the mechanisms of the various reactions are discussed. The phenylquinoline fraction has been investigated in detail and the isomer ratio of the mixture has been evaluated.