Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 8, Issue 22, Pages 5097-5104Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0ob00084a
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Funding
- EaStChem
- EPSRC [GR/S85726/01]
- MIUR, Italy
- Engineering and Physical Sciences Research Council [GR/S85726/01] Funding Source: researchfish
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The reactions of gallium trichloride with phenyl and deuterio-phenyl azides, as well as with 4-methoxyphenyl azide and deuterium isotopomers, were examined by product analysis, CW EPR spectroscopy and pulsed ENDOR spectroscopy. The products included the corresponding anilines together with 4-aminodiphenylamine type dimers, and polyanilines. Complex CW EPR spectra of the radical cations of the dimers [ArNHC6H4NH2](+center dot) S and trimers [ArNHC6H4NHC6H4NH2](+center dot) were obtained. These EPR spectra were analysed with the help of data from the deuterium-substituted analogues as well as the pulse Davies ENDOR spectra. DFT computations of the radical cations provided corroborating evidence and suggested the unpaired electrons were accommodated in extensive pi-delocalised orbitals. A mechanism to account for the reductive conversion of aromatic azides to the corresponding anilines and thence to the dimers and trimers is proposed.
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