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
2,9-dioxabicyclo[4.2.1]Nonan - darstellung, massenspektroskopie und umlagerung eines neuen heterocyclischen systems
作者:Wittko Francke、Wolfgang Reith
DOI:10.1016/s0040-4039(01)92897-7
日期:1981.1
Nine different methyl-substituted compounds of a new acetal system 5 are synthesized from 4-(5-methyl-2-furyl)alkanoles 1 and are rearranged to ketones 6; mass spectroscopic fragmentation patterns are described.