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The characteristics of oxime ethers upon electron‐impact
Author(s) -
Graham Cooks R.,
Varvoglis A. G.
Publication year - 1971
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.1210050607
Subject(s) - chemistry , oxime , intramolecular force , medicinal chemistry , hydrogen atom , electron ionization , derivative (finance) , organic chemistry , stereochemistry , alkyl , ionization , ion , financial economics , economics
The O ‐methyl ethers of aromatic and aliphatic aldoximes and ketoximes are characterized by hydrogen and skeletal rearrangements involving four‐membered cyclic transition states. In the aliphatic compounds, four‐centered rearrangement sometimes yields the species with the higher ionization potential, in contradiction of Audier's rule. The n ‐propyl oxime ethers show a novel skeletal rearrangement involving CH 2 O elimination. The [M—H]+ process in the aromatic aldoxime ethers and an [M—Cl]+ process in an o ‐chloro derivative involve atom elimination by intramolecular aromatic substitution. Aromatic aldoxime ethers and the isomeric nitrones behave completely differently upon electron‐impact.