The fragmentation of ionized alkyl phenyl ethers

Abstract

AbstractThe energetics of olefin loss from ionized alkyl phenyl ethers have been determined by ionization and appearance energy measurements. It is concluded that the reaction is governed by one or more of three features: (i) the strength of the bond between the phenoxy radical and the alkyl ion; (ii) the ease of isomerization of the alkyl ions, chiefly by H‐shifts therein, and (iii) the strength of the CH bond (primary, secondary and tertiary) involved in the H transfer to oxygen which precedes the olefin loss. The possible participation in the reaction of distonic ions and proton bound radical‐molecule pairs is also discussed.