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New fragmentation pathways in the electron impact mass spectrometry of derivatized pyrano‐1,3‐diphenylprop‐2‐enones
Author(s) -
Parmar Virinder S.,
Sharma Sunil K.,
Vardhan Anand,
Sharma Rakesh K.,
Møller Jørgen,
Boll Per M.
Publication year - 1993
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.1210280106
Subject(s) - fragmentation (computing) , electron ionization , chemistry , intramolecular force , mass spectrum , ion , chalcone , polyatomic ion , mass spectrometry , computational chemistry , stereochemistry , medicinal chemistry , photochemistry , ionization , organic chemistry , chromatography , computer science , operating system
The fragmentation patterns of closely related chalcones, cinnamoylchromans and cinnamoylchromenes, are reported to be strikingly different. The mass spectra of the first group show peaks typical of the fragmentation of simple chalcones balanced by additional fragmentation routes competing effectively with the typical chalcone fragmentation. For the other group with the introduced double bond the fragmentation is considerably changed. Initial loss of a methyl group gives rise to formation of the base peak in three of four examples. The [M – CH 3 ] + ion decomposes further, eliminating a styrene yielding the m / z 187 ion. This process may be rationalized as a retro‐Diels–Alder fragmentation of a flavanone formed on intramolecular rearrangement of the molecular ion.