The Generation of New Active Oxygen-Containing Reagents by Chemical and Electrochemical Means

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(1) Baeyer-Villiger Type Oxidation in a Dioxygen-Arenecarbaldehyde-Metal DioxideAerobic Baeyer-Villiger type reaction of cyclic ketones was achieved by using RuO_2, MnO_2, or other transition metal oxides as catalyst in the presence of arenecarbaldehyde, giving the corresponding lactones in good yields.(2) Aerobic Oxidation of Primary Alcohols to Carboxylic Acids and Oxyalkanals in a Hybrid System of TEMPO and Ruthenium ComplexPrimary alcohols were oxidized to the corresponding carboxylic acids through the aldehydes in an oxidizing system composed of 4-BzOTEMPO (0.1 equiv.), RuCl_2 (PPh_3) _3 as a catalyst, and molecular oxygen.Similar reaction of primary alcohols with 4-BzOTEMPO (2 equiv.) leads to concomitant oxidation and substitution, giving the corresponding alpha-oxygenated alkanals. The reaction of secondary alcohols terminates at the stage of oxidation of hydroxyl group, forming the ketones, selectively.