Insights into the temperature-driven competitive pericyclic transformations of allyloxy furan

Abstract

Here, using comprehensive density functional theory calculations augmented by labeling studies, we investigated the mechanistic details of low temperature [3,3]-sigmatropic rearrangement reaction of allyoxy furan and its [4+2]-cycloaddition reaction with acetylene dicarboxylate. In particular, we identify important factors contributing to the low energy requirement of the [3,3]-sigmatropic rearrangement reaction.