PMID: 11929245Apr 4, 2002Paper

Reactions of N-methyl-N-(4-biphenylyl)nitrenium ion with electron-rich arenes: laser flash photolysis and product studies

Journal of the American Chemical Society
Dominic ChiapperinoD E Falvey

Abstract

An arylnitrenium ion, N-methyl-N-(4-biphenylyl)nitrenium ion, was generated through photolysis of 1-(N-methyl-N-4-biphenylyl)amino-2,4,6-trimethylpyridinium tetrafluoroborate, and its reactions with various donor-substituted arenes (e.g., 1,3,5-trimethoxybenzene, mesitylene, 1,4-dimethoxybenzene, hexamethylbenzene, etc.) were examined using product analysis and laser flash photolysis. In general, trapping of the short-lived nitrenium ion by the arenes leads to three types of products: (1) the parent amine, N-methyl-N-4-biphenylylamine; (2) an ortho-adduct, where the ring position ortho to the nitrenium ion center is bonded to the arene ring; and (3) an N-adduct, where the nitrenium ion nitrogen is bonded to the trap. Laser flash photolysis studies show that the rates of these trapping reactions vary from 10(4) to 10(9) M(-1) s(-1), depending on the structure of the arene trap. These trapping rate constants do not correlate with the one-electron oxidation potential of the arene, nor with the expected stability of a sigma-complex derived from direct electrophilic aromatic substitution. It is argued that the observed rate constants correspond to initial formation of a pi-complex between the arylnitrenium ion and the arene trap. Th...Continue Reading

References

Sep 1, 1992·Proceedings of the National Academy of Sciences of the United States of America·W G HumphreysF P Guengerich

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Citations

Sep 6, 2012·Chemical Research in Toxicology·Igor ShamovskyPeter Sjö
Oct 28, 2015·The Journal of Physical Chemistry. B·Jiadan XueDavid Lee Phillips
Mar 30, 2017·The Journal of Organic Chemistry·Kenji MatsumotoMitsuru Shindo
Apr 9, 2014·Chemistry : a European Journal·Esmeralda CaballeroTomás Torres
Jul 23, 2009·The Journal of Physical Chemistry. B·Gregor S PilzakHan Zuilhof
Sep 26, 2017·Journal of the American Chemical Society·Lili DuArthur H Winter
Sep 15, 2006·The Journal of Physical Chemistry. a·P ThanasekaranKuang-Lieh Lu
Apr 13, 2005·The Journal of Organic Chemistry·Andrew C Kung, Daniel E Falvey
Jun 9, 2005·Journal of the American Chemical Society·Pik Ying ChanDavid Lee Phillips
Jun 1, 2007·The Journal of Organic Chemistry·Selina I Thomas, Daniel E Falvey

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