Lone Pair Participation in a Decarboxylation Reaction: A New Design of a Boradecarboxylation Reaction

Abstract

For the mechanism of decarboxylation reactions, all textbooks show electrons moving from the πC=O bond. However, the most electron-donating bond orbital in the carbonyl group is expected to be the lone pair(s) on the oxygen. Thus, orbital theory with delocalization from a lone pair may be more appropriate than delocalization from the πC=O orbital. We confirmed our idea by theoretical calculations. In the TS, if we use 2-substituted

On the mechanism of the peroxide epoxidation of olefins: A bond interaction perspective

“…___________________________________________________ Recently, we demonstrated that orbital theory, where the lone pair on the oxygen plays a role, is more appropriate for describing the decarboxylation reaction than the electronic theory, which is mentioned in almost all textbooks, where an arrow showing movement of the electron is drawn from C=O (Figure 2). 3 Here, we investigate the reaction mechanism in detail from the perspective of bond interaction.…”