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The Claisen rearrangement of protonated allyl phenyl ether
Author(s) -
Kingston Eric E.,
Bey John H.,
Liehr Joachim G.,
Meyrant Philippe,
Flammang Robert,
Maquestiau André
Publication year - 1985
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.1210200507
Subject(s) - protonation , chemistry , carbon monoxide , fragmentation (computing) , ether , dissociation (chemistry) , ion , photochemistry , claisen rearrangement , medicinal chemistry , organic chemistry , catalysis , computer science , operating system
Molecular protonated ions of allyl phenyl ether undergo a Claisen rearrangement both in the ion source and along the flight path. The rearranged ions undergo fragmentation, the predominat loss being ethene, and only a small contribution from loss of carbon monoxide is observed. Collision‐induced dissociation spectra are used to verify the structures of the daughter ions. These spectra, together with other evidence of an acid‐induced ortho rearrangement, allow a mechanism to be proposed for the ethene loss. In contrast, molecular protonated ions of propargyl phenyl ether lose exclusively carbon monoxide.