Photooxygenation of Azidoalkyl Furans: Catalyst-Free Triazole and New Endoperoxide Rearrangement

descriptionPublicationkeyboard_double_arrow_right Article , Other literature type 03 Sep 2013 Turkey English Publisher:American Chemical Society (ACS)Journal:Organic Letters, volume 15, pages 4,790-4,793 (issn: 1523-7060, eissn: 1523-7052,

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Authors: Kazancioglu, Elif Akin; Kazancioglu, Mustafa Zahrittin; Fistikci, Meryem; Secen, Hasan; Altundas, Ramazan;

doi: 10.1021/ol402163u

pmid: 24001310

Photooxygenation of Azidoalkyl Furans: Catalyst-Free Triazole and New Endoperoxide Rearrangement

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Abstract

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%.

Country

Turkey

Related Organizations

Atatürk University
Turkey
Hakkari University
Turkey

Keywords

:NATURAL SCIENCES::Chemistry::Organic chemistry [Research Subject Categories], Molecular Structure, Photochemistry, Carboxylic Acids, Combinatorial Chemistry Techniques, Stereoisomerism, Triazoles, Furans, Catalysis, Peroxides

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