Unexpected Solvolysis of Vitamin A Acetate Under High Pressure Conditions

摘要

Vitamin A acetate was tested for its changes under high pressure. In model solutions of vitamin A acetate in ethanol a Diels-Alder reaction was expected. Instead two ethyl ethers of vitamin A were obtained. Both the all-E-retinylethylether and the 13-Z-retinylethylether are formed via the retinyl-cation as intermediate. The mechanism for such etherifications was well described by C. K. Ingold.