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Stereocontrolled regiospecificity of the water loss from trans ‐sobrerol radical cation upon electron ionization
Author(s) -
Selva Antonio,
Ferrario Francesco,
Ventura Paolo,
Pellegata Renato
Publication year - 1987
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.1210220809
Subject(s) - chemistry , electron ionization , ion , ionization , ionic bonding , epoxide , mass spectrometry , deuterium , kinetic energy , photochemistry , analytical chemistry (journal) , organic chemistry , atomic physics , chromatography , catalysis , physics , quantum mechanics
Water loss from frans‐sobrerol upon electron impact ionization selectively involves the tertiary OH group, predominantly occurring by a stereocontrolled H‐transfer from C(5) position in a rate‐determining step process, as proved by 18 O and deuterium labelling. Monomethyl ethers behave accordingly. Ionic structures of the water‐loss product or products are investigated by metastable ion and collision activation mass‐analysed ion kinetic energy spectroscopy, using model ions generated from some substrates, which are chemically related to fralts‐sobrerol in condensed phase, i.e. α‐pinane epoxide, cis‐sobrerol and pinol. A substantial conversion of cis‐sobrerol molecular ions to ionized pinol by loss of water has been demonstrated.