Angle distortion model for predicting enediyne activation towards Bergman cyclization: an alternate to the distance theory.

ABSTRACT: The kinetics of Bergman cyclization (BC) of enediynes into 1,4-benzene diradicals (also known as p-benzynes) have attracted interest ever since the discovery of natural enediynes which pointed out a surprising reactivity profile difference across enediynes with varying structural architectures. From the analysis of experimental kinetic data, several models were proposed to have a structure-kinetics correlation, out of which, the cd-distance model and the transition state model are the most accepted ones. Recently, Houk et al. introduced a distortion model to explain the regioselectivity of nucleophilic addition to unsymmetrical o-benzynes based on the geometry of the transition state. In the case of BC, since the reaction is endothermic, the transition state geometrica

SUBMITTER: Bhattacharya P 

PROVIDER: S-EPMC9386575 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature