Studies in azide chemistry. Part VI. Some reactions of perfluoroazidobenzene and perfluoro-4-azidotoluene

Publisher Website
Google Scholar
Abstract
Perfluoroazidobenzene readily undergoes the Staudinger reaction with triphenylphosphine, reacts with dimethyl sulphoxide at elevated temperatures to yield a sulphoximide, partakes in 1,3-dipolar cycloaddition reactions with diphenylacetylene, phenylacetylene, cyclopentadiene dimer, norbornene, and acrylonitrile, and, at 130 °C or above, gives the C–H ‘nitrene insertion’ product C6F5·NHPh with benzene, and, inter alia, the N–H ‘nitrene insertion’ products C6F5·N:NPh, C6F5·N:N·C6H4F-p, and C6F5·N:N·C6F5 with aniline, p-fluoroaniline, and pentafluoroaniline, respectively. Perfluoro-4-azidotoluene reacts with dimethyl sulphoxide, cyclohexane, aniline, and pentafluoroaniline at 160 °C to yield ArFN:S(:O)Me2, ArFNH·C6H11, ArFN:NPh + anilino-substituted derivatives, and ArFN:N·C6F5, respectively (ArF=p-F3C·C6F4). The nitrenoid N–H ‘insertion’ reactions provide a new method for the synthesis of unsymmetrical polyfluorinated aromatic azo-compounds.

This publication has 1 reference indexed in Scilit: