Metal–ammonia reduction of an NN-dimethyl-aniline usually gives the cyclohexadiene of type (1). These enamines react with αβ-unsaturated ketones to give initially a 2-substituted cyclohexenone [e.g.(4)] or a hydronaphthalene ketone [e.g.(3)].
A. J. Birch, E. G. Hutchinson and G. S. Rao, J. Chem. Soc. D, 1970, 657 DOI: 10.1039/C29700000657
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