CrO 3 has been found to be an efficient catalyst for benzylic oxidation with periodic acid as the terminal oxidant in acetonitrile. Substituted toluenes with an electron-withdrawing group at the 4-or 3-position and diarylmethanes such as diphenylmethane and fluorene were oxidized to the corresponding substituted benzoic acids and ketones in excellent yields. Benzyl ethers such as isochroman and phthalan were converted to 3,4-dihydroisocoumarin and phthalide in quantitative yields.
Aliphatic primary amines having α-methylene underwent oxidative dehydrogenation on treatment with NiSO4 as a catalyst and K2S2O8 as an oxidant to give the corresponding nitriles in good yields. Benzhydrylamine was converted to benzhydrylideneamine quantitatively under the same reaction conditions.
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