Publication Date:
2012-04-15
Description:
The photochemistry of 2,4,6-triazido-3,5-difluoropyridine 21 was investigated by matrix infrared and electron paramagnetic resonance spectroscopies. Ultraviolet irradiation (〉260 nm) of 21 results in the formation of 3,5-difluoropyridyl-2,4,6-trinitrene 26 in yields high enough for characterization by infrared spectroscopy. The experimental infrared spectrum is in good agreement with density functional theory calculations. Under similar conditions, a very strong electron paramagnetic resonance spectrum of septet trinitrene 26 was obtained. Shorter irradiation times resulted in more complex product mixtures containing, in addition, mononitrenes and dinitrenes. Surprisingly, azirines and keteneimines, the typical photoproducts of arylnitrenes, were not observed. Copyright © 2011 John Wiley & Sons, Ltd. UV irradiation (〉260 nm) of 2,4,6-triazido-3,5-difluoropyridine results in the formation of 3,5-Difluoropyridyl-2,4,6-trinitrene in yields high enough for characterization by IR spectroscopy. The experimental IR spectrum is in good agreement with DFT calculations. Under similar conditions a very strong EPR spectrum of septet the trinitrene was obtained. Shorter irradiation times resulted in more complex product mixtures containing in addition mononitrenes and dinitrenes. Surprisingly, azirines and keteneimines, the typical photoproducts of arylnitrenes, were not observed.
Print ISSN:
0894-3230
Electronic ISSN:
1099-1395
Topics:
Chemistry and Pharmacology
,
Physics
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