4.7 Article

Formation of Enol Ethers by Radical Decarboxylation of α-Alkoxy β-Phenylthio Acids

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 19, Pages 12542-12552

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02042

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Funding

  1. NSERC [0029322]
  2. International Research Support Initiative Program (Pakistan)
  3. SERB Overseas Postdoctoral Fellowship (India)

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Enol ethers are formed by radical decarboxylation of alpha-alkoxy beta-phenylthio acids via the corresponding Barton esters. The phenylthio acids were usually made by the known regioselective reaction of alpha,beta-epoxy acids with PhSH in the presence of InCl3, followed by O-alkylation of the resulting alcohol. In one case, thiol addition to an alpha,beta-unsaturated ethoxymethyl ester was used.

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