Journal of the Chemical Society. Perkin transactions II p. 1649 - 1652 (1991)
Update date:2022-08-02
Topics:
Clarke, Leo F.
O'Sullivan, Fiona
Hegarty, Anthony F.
The E-isomers of aliphatic aldehyde N,N-dimethylhydrazones undergo competing E to Z isomerisation and photolysis to nitriles under UV (254 nm) irradiation.The Z-E isomer mixture which results thermally reverts to the more stable E-Isomer and under short irradiation times the photoisomerisation/thermal reversion cycle can be reversible.Trimethylacetaldehyde N,N-dimethylhydrazone undergoes similar reactions (ruling out the intervention of other types of hydrazone isomerisation) and the rates of the thermal Z->E reactions for RCH=N-NMe2 are in the order R = But > Et > Me.The results are considered in terms of conformations of the hydrazones and the mechanism of E-Z isomerisation.
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Doi:10.1246/bcsj.64.3256
(1991)Doi:10.1021/ja305851h
(2012)Doi:10.1007/BF00948052
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