New mechanistic interpretations for nitrone reactivity

Org Biomol Chem. 2017 Apr 18;15(16):3364-3375. doi: 10.1039/c7ob00429j.

Abstract

The reactivity of nitrones in cycloadditions and related reactions is revisited by introducing a topological perspective. In particular, the study of electron localization function (ELF) along a reaction pathway allows evaluating bond reorganization showing that in several cases the bonds are formed in a sequential way, the second one being formed once the first one is already formed. Both classical 1,3-dipolar cycloadditions and Mannich-type reactions revealed unexpected features often underestimated in classical mechanistic studies.

Publication types

  • Review