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[4+2] Cycloaddition reaction of 1-(cyclopenten-1-y1)-1-morpholino ethene with β-nitrostyrene leads to tetrahydroindan and tetrahydroindanone derivatives. A [4+2] adduct of interest is also obtained in the reaction of the same substrate with mesyl chloride. Reactivity of the same electrophiles with the morpholino enamine of cyclopentyl-methyl ketone is also examined. Some stereochemical aspects of the above mentioned reactions are discussed.

The ionization energy (i.e.) values for electrons in the π MOs of some tertiary amines and enemines derived from morpholine, piperidine and pyrrolidine have been determined by u.v. photoelectron spectroscopy. The effects of structural changes are discussed. The nitrogen lone pair i.e. value is taken as a measure of basicity of amines and enamines in the gas phase. The relative order of basicity is secondary amines < tertiary amines < enamines. This order differs from that found in aqueous solution probably because of solvation effects in the latter.

Polyfunctionalized aromatic urethanes and heterocyclic compounds are obtained from hydrazinosubstituted enaminoketones.

Die AS-Enamine (I) lassen sich mit β-Nitro-styrol (II) stereospezifisch zu den Produkten (III) umsetzen, deren Hydrolyse die cis-erythro-Ketone (IV) ergibt.