75163-12-1Relevant articles and documents
Skeletal Rearrangements on Chemical Ionization of Dibenzyl Ether and Derivatives
Kingston, Eric E.,Shannon, James S.,Diakiw, Vladimir,Lacey, Michael J.
, p. 428 - 440 (2007/10/02)
Protonated molecular ions of dibenzyl ether, formed by chemical ionization using hydrogen and isobutane as reagent gases, undergo skeletal rearrangements to lose water and formaldehyde, both in the ion source and the flight path.The rearrangements have been elucidated by deuterium labelling and chemical substitution.The water lost contains the reagent proton and an aromatic hydrogen atom, and the aromatic hydrogen atoms have been shown to be mobile prior to the reaction.It is proposed that the skeletal rearrangement for water loss is initiated by protonation on the other oxygen atom, followed by benzyl migration.The formaldehyde loss contains benzylic hydrogen atoms exclusively, and it is proposed that the skeletal rearrangement is preceded by hydrogen rearrangement of an oxygen protonated molecular ion to a ring protonated molecular ion.Daughter ion structures are supported by comparisons of their collision induced dissociation spectra with those of isomeric ions prepared by alternative routes.
Mechanism of Anodic Cleavage of Benzyl Ethers
Boyd, Jean W.,Schmalzl, Paul W.,Miller, Larry L.
, p. 3856 - 3862 (2007/10/02)
Kinetic isotope effects and substituent effects are utilized to elucidate the mechanism of the anodic oxidation of benzyl ethers at platinum in acetonitrile.All of the data, including some previously published results, are consistent with a mechanism involving phenylalkoxy carbonium ions.Much of the data is incompatible with a previous mechanistic proposal involving initial oxidative cleavage of the benzyl carbon-oxygen bond.
