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

A new catalyst for Meinwald rearrangement and synthesis of 1,3-dioxolan is proposed for reactions of terminal epoxides as an example. A highly efficient and selective rearrangement in the presence of catalytic quantities of tetraethylammonium iodide was shown. Excellent yields of acetyl derivatives were obtained at this rearrangement. An anomalous condensation of 4-(3,6-dichloro-9-carbazol-9-yl)-3-hydroxybutanenitrile with aldehydes and ketones was discovered. This condensation is accompanied by the elimination of water in an alkaline solution and only derivatives of -butadienes are formed.