Nitration of the methylnaphthalenes

Abstract

The nitration of naphthalene, 1-methylnaphthalene, and 2-methylnaphthalene has been studied under a variety of conditions. Relative rates by competition and isomer distributions have been determined using gas chromatographic analyses. The derived partial rate factors are discussed in terms of various nitration mechanisms and the effect of the methyl group on reactivity in the naphthalene system. A simple route to 1-methyl-8-nitronaphthalene is described.