Formation of 2-cyclohexenones by Friedel-Crafts acylation of alkenes with β,γ-ethylenic acyl halides

Article abstract of DOI:10.1016/S0040-4020(01)86590-X

Friedel-Crafts acylation of alkenes with β,γ-alkenoyl halides leads to conjugated Al-trienolates able to cyclize into Al-enolates of 2-cyclohexenones through an allowed thermal disrotary electrocyclization mechanism. Discussion of the product structures is based on two-dimensional NMR experiments (400 MHz) and molecular mechanics studies (GENMOL and MM2).