The elimination of HCN from the molecular ion of o-nitrobenzyl cyanide under electron impact is shown by deuterium labelling to take place with the abstraction of one of the benzylic hydrogens. This is the first case of a specific 1,1-elimination. o-Nitrobenzyl chloride and o-nitrobenzyl alcohol do not undergo similar eliminations.
A. Kalir, E. Sali and A. Mandelbaum, J. Chem. Soc., Perkin Trans. 2, 1972, 2262 DOI: 10.1039/P29720002262
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