Phenoxazine oxidative dimerization

Fluoride-ion reactions are the most perplexing of all. A fairly large number of anodic fluorinations have been reported in the literature (41). These are anodic oxidations of aromatics and alkenes at potentials well below that of fluoride ion. Yet, examples of fluorination of isolated cation radicals are, so far, very rare. Reaction of fluoride ion with 3 gave 3 (38%), its 3,10 -dimer (13%) and the well-known green dimer cation (jS). In leading to the dimer, fluoride ion has>behaved as a base. For some years it appeared that fluoride ion was too poor a nucleophile to react as in eq. 31, but we believe now that this is not correct. Mass spectrometry has shown that a monofluoro-N-phenyl-phenoxazine dimer is obtained from S " (8). Most recently mass spectrometry has also shown that a small amount of fluoroperylene is formed from lO " ", in contrast with our earlier report ( ). ... 

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