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Mass spectra of aryl substituted oxazolidones
Author(s) -
Auerbach Robert A.,
Minden David L. Von,
Kingsbury C. A.
Publication year - 1970
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.1210040105
Subject(s) - aryl , fragmentation (computing) , substituent , mass spectrum , chemistry , alkyl , metastability , protonation , aldehyde , nitrogen , medicinal chemistry , ion , spectral line , stereochemistry , organic chemistry , physics , catalysis , computer science , operating system , astronomy
Abstract The mass spectra of several 4,5‐disubstituted‐2‐oxazolidones and several related N‐methyl derivatives have been determined. Fragmentation has been found to be a function of three factors: (1) the size of the alkyl function at C‐5, (2) the location of the aryl substituent, and (3) replacement of NH by NCH 3 . In particular, aryl or bulky alkyl groups substituted at C‐5 result in protonated aldehyde derived from hydrogen rearrangement from nitrogen. With other substituents, the most intense ions are nitrogen containing fragments. In the latter case the fragmentation pathway has been elucidated with the aid of metastable peaks observed using defocusing techniques.