The Reaction of CO2 with a Borylnitrene: Formation of an 3-Oxaziridinone

Abstract

The reaction of a borylnitrene with carbon dioxide is studied under cryogenic matrix isolation conditions. Photogenerated CatBN (Cat=catecholato) reacts with CO2 under formation of the cycloaddition product CatBNCO2, a 3-oxaziridinone derivative, after photoexcitation (>550 nm). The product shows Fermi resonances between the CO stretching and ring deformation modes that cause unusual 13C and 18O isotopic shifts. A computational analysis of the 3-oxaziridinone shows this cyclic carbamate to be less strained than an α-lactone or an α-lactame.