Interconversion of Nitrenes, Carbenes, and Nitrile Ylides by Ring Expansion, Ring Opening, Ring Contraction, and Ring Closure: 3-Quinolylnitrene, 2-Quinoxalylcarbene, and 3-Quinolylcarbene

@article{Kvaskoff2009InterconversionON,
  title={Interconversion of Nitrenes, Carbenes, and Nitrile Ylides by Ring Expansion, Ring Opening, Ring Contraction, and Ring Closure: 3-Quinolylnitrene, 2-Quinoxalylcarbene, and 3-Quinolylcarbene},
  author={D. Kvaskoff and U. Mitschke and C. Addicott and J. Finnerty and P. Bednarek and C. Wentrup},
  journal={Australian Journal of Chemistry},
  year={2009},
  volume={62},
  pages={275-286}
}
Photolysis of 3-azidoquinoline 6 in an Ar matrix generates 3-quinolylnitrene 7, which is characterized by its electron spin resonance (ESR), UV, and IR spectra in Ar matrices. Nitrene 7 undergoes ring opening to a nitrile ylide 19, also characterized by its UV and IR spectra. A subsequent 1,7-hydrogen shift in the ylide 19 affords 3-(2-isocyanophenyl)ketenimine 20. Matrix photolysis of 1,2,3-triazolo[1,5-c]quinoxaline 26 generates 4-diazomethylquinazoline 27, followed by 4-quinazolylcarbene 28… Expand
18 Citations
Nitrenes, carbenes, diradicals, and ylides. Interconversions of reactive intermediates.
  • C. Wentrup
  • Chemistry, Medicine
  • Accounts of chemical research
  • 2011
Flash Vacuum Pyrolysis of Azides, Triazoles, and Tetrazoles.
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