Addition reactions of conjugated double bonds. Part V. Stereochemistry of pyrazoline ring formation from αβ-unsaturated phenylhydrazones
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 7,p. 936-938
- https://doi.org/10.1039/p29730000936
Abstract
The stereochemistry of cyclisation of the phenylhydrazones of some αβ-unsaturated ketones is discussed in terms of a stereoselective enamine–imine tautomerism step. Cyclisation of the phenylhydrazone of 1-acetyl-4-t-butyl-cyclohexene results in an initial axial attack of the nitrogen nucleophile on the six-membered ring.Keywords
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