Gas phase anionic ipso substitution reactions of some alkyl phenyl ethers

Article abstract of DOI:10.1016/S0040-4039(00)77787-2

It is shown by ¹⁸O labelling that phenoxide anions are formed both by an S_N2 and a nucleophilic aromatic substitution mechanism in the reaction of OH^- with methyl phenyl ether. These mechanisms are of minor importance in the ethyl phenyl ether system where phenoxide anions are generated almost exclusively by an E₂ mechanism.