Dinitrogen oxide was employed as a clean oxidant for various oxidations in the presence of a catalytic amount of dioxoruthenium tetramesitylporphyrin complex (Ru(tmp)(O)2). A variety of olefins, secondary alcohols, and benzyl alcohols were smoothly oxidized to the corresponding epoxides, ketones, and aldehydes in high yields. In the oxidation of 9,10-dihydroanthracene derivatives, the competitive reactions affording anthraquinones and anthracenes could be regulated by the reaction conditions. At a high temperature (200°C), anthraquinones were selectively produced, while the anthracenes were selectively produced by the addition of sulfuric acid.
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