By WALTER S. TRAHANOVSKY (Eds.)
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Extra info for Oxidation in Organic Chemistry, Part B
Example text
Chem. Soc. 89, 4176 (1967). Μ. Μ. T. Khan and A. E. Martell, / Amer. Chem. Soc. 89, 7104 (1967). Y. Ogata, Y. Kosugi, and T. Morimoto, Tetrahedron 24, 4057 (1968). Y. Ogata and Y. Kosugi, Tetrahedron 25, 1055 (1969). L. Pekkarinen and L. Lieto, Suom. Kemistilehti Β 43, 242 (1970). L. Pekkarinen, Suom. Kemistilehti Β 43, 305 (1970). R. Griesser, B. Prijs, and H. Sigel, / . Amer. Chem. Soc. 91, 7758 (1969). /. Oxidation by Cupric Ion 51 231-234 The copper(II)-catalyzed autoxidation of b e n z o i n and ascorbic acid is complicated by the presence of hydrogen peroxide which is produced under certain conditions.
H. James and A. Weissberger, / . Amer. Chem. Soc. 59, 2040 (1937). 52 W. G. NIGH amine, the initial product is presumably the α-imino ketone which is rapidly hydrolyzed to the diketone under the reaction conditions. In contrast to the aliphatic case, primary aromatic amines are readily oxidized to azobenzenes by cuprous chloride and oxygen when pyridine is used as the s o l v e n t . Collidine and 2-picoline may be substituted for pyridine, but with a resulting decrease in the rate of reaction.
This behavior suggests that the amine undergoes a one-electron oxidation to a free-radical intermediate which then dimerizes to the hydrazo compound. Since the spectroscopic results of van Heuvelen and Goldstein indicate that a fairly strong covalent bond is formed between aniline and copper(II), it seems reasonable to assume that the oxidation involves the initial formation of a complex. The transfer of an electron from the ligand to the metal ion would generate the required free-radical intermediate.