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A novel rearrangement in the gas phase under electron ionization for 3‐glycosyl‐5‐aryl‐2‐isoxazolines
Author(s) -
D’Accorso Norma,
Fascio Mirta,
Arabehety Carlos Gustavo,
Seldes Alicia M.
Publication year - 1999
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/(sici)1096-9888(199909)34:9<915::aid-jms850>3.0.co;2-a
Subject(s) - chemistry , aryl , electron ionization , fragmentation (computing) , substituent , bond cleavage , glycosyl , ring (chemistry) , mass spectrometry , derivative (finance) , gas phase , tandem mass spectrometry , medicinal chemistry , stereochemistry , computational chemistry , photochemistry , ionization , organic chemistry , ion , alkyl , chromatography , computer science , financial economics , economics , catalysis , operating system
Some 3‐glycosyl‐5‐aryl‐2‐isoxazolines were studied in the gas phase under electron ionization (EI) conditions in order to elucidate their behavior. These derivatives showed an interesting rearrangement involving opening of the heterocyclic ring with a concomitant ring closing to afford a new isoxazoline derivative. The first step of this reaction was the less common cleavage of the heterocyclic C(5)—O bond. The 5‐aryl substituent was responsible for the pseudobenzylic stabilization of the new isoxazoline derivative. EI tandem mass spectrometry and EI high‐resolution mass spectrometry allowed the elucidation of fragmentation pathways. Copyright © 1999 John Wiley & Sons, Ltd.