Photochemical isomerization of 7-aryl-substituted 1H-Azepin-2(3H)-ones. Formation and X-ray structure determination of atropisomeric ketimines

Abstract

The structures of two isomeric 3,5-di-t-butyl-2-[(3,5-di-t-butyl-2-hydroxyphenyl){(Z)-methylimino}- methyl]cyclopent-2-en-1-ones, formed upon photoexcitation of 3,5-di-t-butyl-7-(3,5-di-t-butyl-2- hydroxyphenyl)-1-methyl-1H-azepin-2(3H)-one in methanol, have been established by X-ray diffraction, and are found to be examples of atropisomeric ketimines. In both isomers, the geometry of imino substitution is characterized by intramolecular hydrogen bonding with the phenolic hydroxyl.