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.
H. Ferres, M. S. Hamdam and W. R. Jackson, J. Chem. Soc., Perkin Trans. 2, 1973, 936 DOI: 10.1039/P29730000936
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