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Pyrones: V—The mass spectra and fragmentation mechanisms of some 3(5)‐methoxy‐4‐pyrones
Author(s) -
McGillivray David L.,
Poulton Gerald A.
Publication year - 1980
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.1210150110
Subject(s) - mass spectrum , fragmentation (computing) , chemistry , substituent , deuterium , polyatomic ion , spectral line , stereochemistry , hydroxymethyl , ion , computational chemistry , medicinal chemistry , organic chemistry , physics , quantum mechanics , astronomy , computer science , operating system
The mass spectra of methyl kojate (2‐hydroxymethyl‐5‐methoxy‐4 H ‐pyran‐4‐one), two deuterated analogues and 14 related 3(5)‐methoxy‐4‐pyrones have been studied. These compounds fragment according to a common mechanism, initiated by primary rearrangement of the molecular ion(s). Guidelines which indicate the presence of 3(5)‐methoxy‐4‐pyrones and allow structural determinations to be made from their mass spectra are presented. For the majority of substituents studied, the nature of the substituent has no major effect upon the fragmentation pattern; the cyano group does. The hydroxy counterparts of the above compounds are readily converted for analysis by simple methylation.