PMID: 9416466Jan 7, 1998Paper

Reaction of substituted anthracenes and a butadiene with nitric oxide: product formation determined by EPR spectroscopy

Free Radical Research
D PfeilerG R Hanson

Abstract

When nitric oxide (NO), generated from nitric acid and copper, was reacted with a series of 9,10-substituted anthracenes, only 9,10-dimethylanthracene gave EPR detectable nitroxide radicals, although the expected bicyclic nitroxide arising from cheletropic NO addition across the 9,10-positions was not observed. Purity of the NO is crucial as the presence of higher oxides of nitrogen leads to radicals by hydrogen abstraction which are trapped by NO and the resultant nitroso compounds produce stable nitroxides detectable by EPR. In contrast the acyclic system, 3,4-diphenyl-2,5-dimethyl-2,4-hexadiene gives rise to an EPR spectrum consistent with cheletropic NO addition, although higher oxides of nitrogen again mediate the formation of different nitroxides.

References

Dec 28, 1992·Science·E Culotta, D E Koshland
Dec 1, 1987·Proceedings of the National Academy of Sciences of the United States of America·L J IgnarroG Chaudhuri
Feb 1, 1993·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·S Archer
Apr 25, 1996·Biochemical and Biophysical Research Communications·V QuaresimaH Utsumi

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Citations

Jul 3, 2018·Microfluidics and Nanofluidics·Jin Woo LeeJacob Lutz
Jul 21, 2009·Chemical Reviews·Jens Hartung

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