Journal of Organic Chemistry p. 2544 - 2550 (1986)
Update date:2022-08-11
Topics:
Galen, Dean A. Van
Barnes, James H.
Hawley, M. Dale
Fluorenone tosylhydrazone (Fl=NNHTs) undergoes one-electron reductive dehydrogenation in DMF-0.1 F (n-Bu)4NClO4 to give hydrogen and its conjugate base Fl=NN-Ts as products.Fl=NN-Ts is subsequently reduced at more negative potential to a dianion radical (Fl=NNTs dianion radical) that is stable on the cyclic voltammetric time scale.On the coulometric time scale or in the presence of added proton donors (pKa < ca.29), Fl=NNTs dianion radical decomposes to give FlHNH2 and TsNH2 as the principal products.A pathway is proposed for the reaction of Fl=NNTs dianion radical which involves rate-determining proton abstraction by the nitrogen atom α to the fluorene moiety.Cyclic voltammetric and chronoamperometric data are presented which are consistent with the formation of the tosyl nitrene anion radical as a short-lived, unobserved intermediate.
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