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TEMPO-Catalyzed Direct Conversion of Primary Alcohols to α‑Chloroacetals with TCCA Both as an Oxidant and a Chlorination Reagent

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journal contribution
posted on 2018-08-13, 14:39 authored by Guangyuan Feng, Suliu Feng, Lei Liu, Haitang Du, Chunbao Li
Multistep reactions are often required for the transformation of alcohols to α-chloroacetals via the unstable intermediates aldehydes or α-halo aldehydes. Herein, we report a simplified procedure for practical synthesis of α-chloroacetals using 2,2,6,6-tetramethylpiperidine-1-oxyl as a catalyst and trichloroisocyanuric acid both as an oxidant and a chlorination reagent. The reaction is one-pot, solvent-free and high-yielding. In addition, the α-chloroacetals have been transformed to enol ethers through the elimination reaction in the presence of sodium.