Evidence is presented which suggests that deprotonated hydrazones undergo a negative ion Beckmann rearrangement, for example, –CH2(Me)C![[double bond, length half m-dash]](https://www.rsc.org/images/entities/char_e006.gif)
NNMe2→[(CH2CNMe)Me2N–]↔[(CH2CNMe)˙–Me2N˙–]→–CH2CN + Me3N. A number of fragmentations not involving skeletal rearrangement are also observed including a characteristic elimination of methane, e.g.–CH2(Me)CNNMe2→[(CH2(Me)C–NNMe)Me–]→ CH2(Me)C–NNCH2–+ CH4.
G. W. Adams, J. H. Bowie, R. N. Hayes and M. L. Gross, J. Chem. Soc., Perkin Trans. 2, 1992, 469 DOI: 10.1039/P29920000469
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