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

ABSTRACT: Multistep reactions are often required for the transformation of alcohols to ?-chloroacetals via the unstable intermediates aldehydes or ?-halo aldehydes. Herein, we report a simplified procedure for practical synthesis of ?-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 ?-chloroacetals have been transformed to enol ethers through the elimination reaction in the presence of sodium.

SUBMITTER: Feng G

PROVIDER: S-EPMC6644693 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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

Feng Guangyuan G Feng Suliu S Liu Lei L Du Haitang H Li Chunbao C

ACS omega 20180813 8

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 ...[more]

PMID: 31459035

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