Hydrazine derivatives. Part II. Oxidation of aldehyde NN-disubstituted hydrazones with lead tetra-acetate
- 1 January 1970
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 10,p. 1494-1497
- https://doi.org/10.1039/j39700001494
Abstract
The oxidation of a number of arenecarbaldehyde NN-disubstituted hydrazones with lead tetra-acetate proceeds in two steps. The first involves carbon–nitrogen bond cleavage to give an aldehyde and an arenecarbaldehyde monohydrazone. The second involves further oxidation of the monohydrazone to a diacylhydrazine. The order of ease of cleavage of alkyl groups was found to be p-methoxybenzyl > benzyl > p-chlorobenzyl methyl. A mechanism has been suggested for the cleavage reaction. The oxidation of the monohydrazone proceeds via a nitrilimine.Keywords
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