Hydrazine derivatives. Part II. Oxidation of aldehyde NN-disubstituted hydrazones with lead tetra-acetate

J.B. Aylward

Document Type

Article

Publication Date

1-1-1970

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 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

Hydrazine derivatives, Oxidation, aldehyde NN-disubstituted hydrazones, tetra-acetate

Divisions

CHEMISTRY

Publication Title

Journal of the Chemical Society C: Organic

Volume

10

Publisher

Royal Society of Chemistry

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