Deuterium reduction (Pd–BaSO4) of NN-dimethylpropargylammoniobenzamidate to N-(2,3-dideuterioallyl)dimethylammoniobenzamidate and thermal rearrangement of the latter to N-(1,2-dideuterioallyl)-N′N′-dimethylbenzohydrazide validates a concerted [3,2] rearrangement for unsubstituted allyl groups in this series. Thermolysis of related hydrazinium halides gives the dialkylhydrazides.
I. D. Brindle and M. S. Gibson, J. Chem. Soc., Perkin Trans. 1, 1979, 517 DOI: 10.1039/P19790000517
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