期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 70, 期 8, 页码 3127-3132出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo0477749
关键词
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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) with time-resolved IN-vis (TRUV) detection as well as photoproduct analysis verified that the expected nitrenium 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 to other arylnitrenium ions is discussed in terms of steric and electronic effects.
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