Functionalization of Terminal Epoxides. Tetraethylammonium Iodide-Catalyzed Meinwald Rearrangement and Synthesis of 1,3-Dioxolane

A new efficient catalyst has been proposed for the Meinwald rearrangement of terminal epoxides with the formation of 1,3-dioxolane derivatives. Terminal epoxides have been converted in high yields into acetonyl derivatives in the presence of a catalytic amount of tetraethylammonium iodide. Anomalous condensation of 4-(3,6-dichloro-9H-carbazol-9-yl)-3-hydroxybutanenitrile with aldehydes and ketones in alkaline medium has been revealed. This condensation is accompanied by elimination of water and yields exclusively products with a Z-butadiene fragment.