| Abstract
| - N-Methyl-N-1-naphthylnitrenium ion (2) was generated through photolysis of 1-(N-methyl-N-(1-naphthyl)amino)-2,4,6-trimethylpyridinium tetrafluoroborate (1). Laser flash photolysis (LFP) withtime-resolved UV−vis (TRUV) detection as well as photoproduct analysis verified that the expectednitrenium ion was formed cleanly and rapidly following photolysis. Consistent with an earlier study,which used competitive trapping methods (Novak, M. et al. J. Org. Chem.1999, 64, 6023−6031),it is found that 2 reacts rapidly with a variety of nucleophiles. The high reactivity of 2 relative toother arylnitrenium ions is discussed in terms of steric and electronic effects.
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