Pyrolysis of benzophenone oxime carbonates: a potential route to aryl imino ethers (aryl imidates)

Abstract

Aryl ketoxime carbonates have been found to undergo decompositions at temperatures ranging from 180–200°C to give carbon dioxide and aryl imino ethers (imidates). This pyrolysis could prove to be a general method for preparing aryl imino ethers. Formation of different imidates from the two geometric isomers (E- and Z-forms) of the ketoxime carbonates supports a mechanism involving the migration of the aryl group trans to the carbonate grouping. This is similar to that observed in the Beckmann rearrangement of ketoximes.