6533b832fe1ef96bd129ac84

RESEARCH PRODUCT

A new general fragmentation reaction in mass spectrometry: The hydrogen-carbon, carbon-carbon double rearrangement of 2 heteroalkyl substituted diphenylmethyl cations

Liliana LamartinaMirella FerrugiaPasquale AgozzinoMaria Concetta NatoliLeopoldo Ceraulo

subject

inorganic chemicalsCollision-induced dissociationHydrogenChemistryHydrideorganic chemicalsPolyatomic ionReinforced carbon–carbonAnalytical chemistrychemistry.chemical_elementMass spectrometryMedicinal chemistryIonFragmentation (mass spectrometry)heterocyclic compoundsSpectroscopy

description

Diphenylmethyl cations formed by benzylic cleavage of the molecular ions of ortho heteroalkyl substituted 1,1-diphenylalkanes undergo the double rearrangement process (H to C followed by C to C) previously reported for ortho-methoxy derivatives. Hence the formation of substituted benzyl (or tropylium) ions allowing this double rearrangement process constitutes an interesting type of fragmentation reaction characteristic for 1,1-diphenylalkanes bearing ortho substituents (OMe, OEt, OiPr, SMe, NHMe, NMe2) which are able to transfer a hydride to the charged benzyl carbon of diphenylmethyl cations formed by benzylic cleavage of the molecular ion.

https://doi.org/10.1255/ejms.162