FORMATION OF MONOALDEHYDES BY CERIUM(IV) AMMONIUM NITRATE OXIDATION OF UNSYMMETRIC DIMETHYLNAPHTHALENES

Article abstract of DOI:10.1016/S0040-4020(01)96768-7

When 1,2-,1,3-and 1,6-dimethylnaphthalene are oxidized by Ce(4+) in acetic acid the corresponding monoaldehydes are formed in better than 80percent yield.In each case aldehyde formation takes place with a high degree of selectivity as the methyl-1-to methyl-2-naphthaldehyde ratio is better than 11:1.The selectivity may be explained from differences in reactivity as calculated within the frontier orbital method.