ISSN:
0030-493X
Schlagwort(e):
Chemistry
;
Analytical Chemistry and Spectroscopy
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
The high-resolution mass spectra of two stable enol tautomers, 4,6-diethanoyl-1-methyl-5-phenyl-3-cyclohex-ene-1,3-diol (2) and 4-ethanoyl-5-hydroxy-2-(1-hydroxyethylidene)-5-methyl-3-phenylcyclohexanone (3), and the corresponding diketone tautomer, 2,4-diethanoyl-5-hydroxy-5-methyl-3-phenylcyclohexanone (1), are reported. Collisional activation of the molecular ions and major ionic fragments is used to assign decomposition pathways and to compare ion structures. Ionized 1 and 2 do not interconvert by a keto-enol tautomerism, but isomerize to a common intermediate. This isomerization probably involves opening of the cyclohexanone ring and transfer of the enolizable hydrogen, and is followed by elimination of water. The radical cation of 3 does not interconvert with [1]+· and [2]+· Instead, [3]+· dissociates by loss of an acetyl radical and eliminates water via a higher-energy pathway. As a result, the mass spectra of 1 and 2 are similar, whereas the mass spectrum of 3 is unique.
Zusätzliches Material:
1 Ill.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/oms.1210210907
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