Tetrahedron

Formation of monoaldehydes by cerium (IV) ammonium nitrate oxidation of unsymmetric dimethylnaphthalenes

LK Sydnes, SH Hansen, IC Burkow, LJ Saethre

文献索引：Sydnes, Leiv K.; Hansen, Sissel H.; Burkow, Ivan C.; Saethre, Leif J. Tetrahedron, 1985 , vol. 41, # 22 p. 5205 - 5208

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被引用次数: 11

摘要

When 1, 2-, 1, 3-and 1, 6-dimethylnaphthalene are oxidized by Ce4+ in acetic acid the corresponding monoaldehydes are formed in better than 80% 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.