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Isomerization of [C 6 H 5 C 3 H 5 O] + ˙ ions: The case of 1‐phenylpropenol
Author(s) -
Denhez J. P.,
Audier H. E.
Publication year - 1984
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.1210190902
Subject(s) - isomerization , fragmentation (computing) , ion , chemistry , ketene , hydrogen , bicyclic molecule , kinetic energy , labelling , photochemistry , radiochemistry , stereochemistry , physics , medicinal chemistry , organic chemistry , catalysis , biochemistry , quantum mechanics , computer science , operating system
Appearance energy and kinetic energy release measurments together with isotopic labelling have shown that the meastable molecular ion of 1‐phenylpropenol isomerizes into those of cinnamic alcohol and 3‐phenylpropanal prior to loss of ketene. 13 C labelling and thermodynamic considerations prove that the rearrangement of 1‐phenylpropenol occurs by an ‘ ortho attack’ leading to bicyclic intermediates. Statistical hydrogen exchanges are observed prior to fragmentation. The isomerization mechanisms are discussed.