Electrophilic aromatic reactivities via pyrolysis of 1-arylethyl esters. Part 16. The effects of the acetoxy and acylamino substituents

Abstract

The rates of gas-phase elimination of acetic acid from the appropriate 1-arylethyl acetates have been measured to determine σ⁺ values for the following substitutents: p-OAc (–0.12), m-OAc (0.335), p-NHAc ( [graphic omitted] –0.62), m-NHAc (0.08). The numerical values, and the differences between them and those reported for molecular chlorination, are discussed in terms of electronic effects.