Abstract

The readily available methyl 3,3-dimethylcyclopropene-1-carboxylate undergoes [2+2] cycloaddition with enamines to give 2-aminobicyclo [2.1.0] pentane derivatives in moderate to good yields. These compounds are quantitatively transformed into 3-cyclopentenols by treatment with dilute mineral acids. From enamines derived from medium-ring ketones and morpholine, tricyclic adducts are formed, which eliminate morpholine under flash-thermolysis conditions at 600 o C to give macrocycles containing an E double bond and an allenic system

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