Published January 1, 2013 | Version v1
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Photooxygenation of Azidoalkyl Furans: Catalyst-Free Triazole and New Endoperoxide Rearrangement

  • 1. Ataturk Univ, Dept Chem, TR-25240 Erzurum, Turkey

Description

Photooxygenation of azidoalkyl furans has revealed both a novel triazole formation method and a unique endoperoxide rearrangement. The key step of this method is a 3 + 2 cycloaddion of the azide to the endoperoxide intermediate. The reduction of the peroxide bond and two subsequent C-C bond cleavages provide a triazole having a newly formed carboxylic acid functionality. The reactions are clean and efficient with yields ranging from 60% to 90%.

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