97% conversion was obtained using Mn(OTf) 2 as catalyst, which was adopted for further optimization. Employing LiCl or NaCl as the chloride source was detrimental to conversion, presumably due to decreased solubility in MeCN/AcOH (entries 12 and 13). Gratifyingly, the quantities of MgCl 2 and Mn(OTf) 2 could be lowered to 2 equivalents and 5 mol %, respectively, without significant reduction in conversion (entries 14 and 15). A Faradaic efficiency of 67% was obtained when 2 F/mol of charge was passed (entry 16), which indicated that most of the electricity passing through the cell is utilized productively. The full scope of the electrochemical process was explored starting with the deconstructive chlorination of cyclobutanols to form γ-functionalized ketones (Scheme 2A). From the outset, it was found that 1-arylcyclobutan-1-ols containing aromatic systems with electron-releasing groups at the 2-or 4-positions (e.g. 4-tBu) or extended π systems (e.g. 4-Ph) undergo decomposition using the optimized reaction conditions (Table , entry 11). This instability was attributed to ionization of the C-OH bond in the presence of Brønsted and/or Lewis acids, forming stabilized carbocations that are unproductive for the desired transformation. In such cases, this issue was addressed by employing syringe pump addition of the substrate over 2 h and using TBAOAc as the supporting electrolyte. With a choice of two suitable reaction conditions in hand, a variety of 1arylcyclobutan-1-ols were converted to the corresponding γchlorinated ketone products in good to excellent isolated yields (products 2-20). Within the aryl unit, various alkyl and aryl substitution was tolerated at the 4-, 3-and 2-positions in addition to halides and electron-withdrawing substituents (e.g. 4-CF 3 ). The electrochemical method exhibits good functional group tolerance as demonstrated by the presence of aldehyde, carboxylic acid, methyl ester, primary amide, nitrile, benzylic primary alcohol and silyl ether functionalities present within products 14-20. A selection of 1-alkylcyclobutan-1-ols were also converted into the corresponding γ-chlorinated ketones in good isolated yields (products 21-26). Benzo-fused cyclobutanols participated in deconstructive chlorination, giving benzyl chloride products 27-31, including the formation of 7-, 8-, 9and 10-membered rings. This strategy was also applied to the formation of disubstituted cycloheptane 32 in 77% isolated yield. Additional substitution at the 2-and 3-positions of the cyclobutanol was tolerated, accessing γ-chlorinated ketones 33-35 in high yields. We also investigated the deconstructive chlorination of cyclopropanols (Scheme 2B). Gratifyingly, it was found that a representative selection of 1-arylcyclopropan-1-ols and 1-alkylcyclopropan-1-ols could be readily converted to the corresponding β-chlorinated ketones in good yields (36-39). Additional substitution is tolerated within the cyclopropanol, giving secondary radical derived product 40 as the major regioisomer. Furthermore, bicyclo [4.1.0]heptan-1-ol was converted to 3-chlorocycloheptan-1-one 41 in 48% isolated yield. At the current stage of development, the electrochemical method does not tolerate larger ring sizes with reduced ring strain. For example, despite assessing various reaction conditions, 1phenylcyclopentan-1-ol underwent decomposition, whereas 1phenethylcyclopentan-1-ol was unreactive. In order to demonstrate scalability, the batch process was translated to a flow electrochemical setup. Employing the commercially available Ammonite8 flow electroreactor, a variety of reaction parameters were evaluated including electrolyte loading, temperature, solvent ratio, residence time, charge and mixing efficiency (Scheme 2C). However, using MnCl 2 .4H 2 O (10 mol %) as catalyst, the conversion to 2 could not be increased beyond 20% using single-pass flow electrochemistry. The yield was increased by applying the optimized reaction parameters to a recirculating flow electrochemical setup, which provided access to 2 in 84% isolated yield (Scheme 2D). Advantageously, due to the decreased distance between the electrodes in flow, a supporting electrolyte was not required. Furthermore, by employing a 6-port 2-position switching valve, the flow could be redirected from recirculation to continuous inline purification (Scheme 2E). Once the electrochemical reaction was complete, the valve was switched from position 1 to position 2 to redirect the flow into the path of work-up solvents. The flow was passed through a mixing unit before entering a liquid/liquid phase separator containing a hydrophobic membrane that allowed separation of the organic layer, which was subsequently dried over MgSO 4 , filtered and concentrated in vacuo to provide 1.2 g of product. This flow setup, which combines recirculating flow electrochemistry and continuous inline purification for the first time, enabled the electrochemical process to be performed on gram scale.