EZ-isomerism in alkyl phenyl ketone phenylhydrazones and acetaldehyde phenylhydrazone
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 456-458
- https://doi.org/10.1039/p19760000456
Abstract
The E- and Z-isomers of the hydrazones PhRCN·NHPh (R = Pri or But) exhibit anomalous n.m.r. spectra owing to the C-phenyl group being non-coplanar with the CN bond. An improved procedure for the preparation of pure Z-acetaldehyde phenylhydrazone, the kinetically controlled product of the condensation, is described. Phenyl-hydrazine is shown to catalyse the interconversion of the E- and Z-isomers of phenylhydrazones by an addition–elimination mechanism.Keywords
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