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This concept is utilized to formally insert molecular oxygen after direct or DDQ\u2010assisted anodic oxidation of the strained carbocycles, delivering \u03b2\u2010 and \u03b3\u2010hydroxy ketones and 1,2\u2010dioxanes electrocatalytically. Furthermore, insights into the mechanism of the oxidative process, obtained experimentally and by additional quantum\u2010chemical calculations are presented. 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