title: Photooxygenation of azidoalkyl furans: catalyst-free triazole and new endoperoxide rearrangement.
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%.
authors.affiliation: Department of Chemistry, Ataturk University , 25240 Erzurum, Turkey.
authors.forename: Elif Akin
authors.initials: EA
authors.lastname: Kazancioglu
authors.forename: Mustafa Zahrittin
authors.initials: MZ
authors.lastname: Kazancioglu
authors.forename: Meryem
authors.initials: M
authors.lastname: Fistikci
authors.forename: Hasan
authors.initials: H
authors.lastname: Secen
authors.forename: Ramazan
authors.initials: R
authors.lastname: Altundas
mesh_terms: D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D010545:Peroxides / Q000737:chemistry*; D010777:Photochemistry; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002264:Carboxylic Acids; D005663:Furans; D010545:Peroxides; D014230:Triazoles