Iron lewis acid catalyzed reactions of phenyldiazomethane with aromatic aldehydes

Article abstract of DOI:10.1016/S0040-4020(97)10287-3

The iron Lewis acid 1 was found to catalyze reactions of phenyldiazomethane and aromatic aldehydes to give cis-epoxides along with the corresponding ketones. The yield of the epoxide increased with electron- withdrawing substituents on the aldehyde, while little or no epoxide was formed with electron-donating substituents. The reaction was found to go through the coordination of the aldehyde to the iron Lewis acid instead of a carbene intermediate.