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Electron Impact Induced Loss of C‐5/C‐8 Substituents of 1,2,3,4‐Tetrahydroisoquinolines, V: Synthesis and Mass Spectrometric Fragmentation of Dihydroisoindole Derivatives
Author(s) -
Knefeli Frank,
Mayer Klaus K.,
Wiegrebe Wolfgang
Publication year - 1989
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19893220708
Subject(s) - chemistry , electron ionization , fragmentation (computing) , substituent , mass spectrum , ion , mass spectrometry , medicinal chemistry , stereochemistry , organic chemistry , chromatography , ionization , computer science , operating system
C‐8‐substituted N‐methyl‐1,2,3,4‐tetrahydroisoquinoline radical cations lose the complete substituent in a one step reaction giving rise to an unexpected ion at m/z 146, which is probably identical with the dihydroisoindolyl‐methyl‐cation A . The dihydroisoindoles 1 , 10 , and 16 were prepared as potentially alternative precursors of ion A . However, the ion at m/z 146 in their El mass spectra is of very low intensity, so CID‐experiments for structural comparison could not be performed. The electron impact induced fragmentations of 1 , 10 , and 16 are discussed.