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Electron impact induced migrations of aryl groups in substituted 4(3 H )‐quinazolinones
Author(s) -
Tureček František,
Světlík Jan
Publication year - 1981
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210160702
Subject(s) - aryl , chemistry , metastability , ion , deuterium , mass spectrum , cleavage (geology) , electron ionization , medicinal chemistry , ring (chemistry) , group (periodic table) , stereochemistry , crystallography , organic chemistry , materials science , physics , atomic physics , alkyl , fracture (geology) , composite material , ionization
Electron impact mass spectra of 2‐diphenylmethyl‐3‐aryl‐4(3 H )‐quinazolinones display ions arising from migrations of different aryl groups in the molecular and [MH] + ions. The most abundant ion due to rearrangement, [C 13 H 9 NO] +˙ , is formed by migration of a phenyl from the benzhydryl group onto N‐1 and subsequent cleavage of the heterocyclic ring. Other rearrangements involve initial migration of the N‐3 aryl group to the benzylic carbon. The mechanisms of migrations were elucidated by means of deuterium and 15 N labelling and are supported by metastable spectra.