Water loss from molecular protonated ions of benzyl 2-phenylethyl ether and derivatives

The skeletal rearrangement for water loss is the dominant ion reaction in the chemical ionization mass spectrum of benzyl 2-phenylethyl ether. Isotopic distributions obtained for this reaction with specifically labelled derivatives have been interpreted in terms of competing five- and six-centred skeletal rearrangements. Chemical substitution of the alternative aromatic rings strongly influences the balance of the competition.