Organic electrochemistry represents one of the cleanest possible chemical processing technologies, which has recently undergone a renaissance due partly to the increasing availability of standardized batch and flow electrochemical reactors. By careful tuning of electrochemical parameters, specific single electron transfer processes can be targeted, accessing powerful radical intermediates. Despite these characteristics, the development of an electrochemical method for the generation of alkoxy radicals from alcohols remains an unsolved problem. To this end, herein we report the manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols via alkoxy radical intermediates, 16 accessing synthetically useful β-and γ-Scheme 1. Context and Outline of Electrochemical Strategy chlorinated ketones (Scheme 1C). Furthermore, by employing microreactor technology and recirculating flow, the electrochemical method can be performed on gram-scale, with continuous inline purification incorporated.