How does an alkoxy group at the benzylic carbon affect the transition state of the hydrogen-atom abstraction reaction? Correlation analysis of relative rates for 14 p-Y-substituted α,α-ethylenedioxytoluenes

Abstract

Correlation analysis of the relative rates for the H-atom abstraction reaction of 14 2-(4-Y-phenyl)dioxolanes (p-Y-substituted α,α-ethylenedioxytoluenes, 1-Y) by N-bromosuccinimide (NBS) shows that the spin-delocalization effect is also operating at the transition state of the H-atom abstraction reaction and that the ethylenedioxy group at the benzylic carbon makes the spindelocalization more observable than do two methyl groups.