Sven Fuermeyer et.al.: Detection of Transient Radical Cations in Electron
Transfer Initiated Diels-Alder Reactions by Electrospray Ionization Mass
Spectrometry
- Author(s): Sven
Fuermeyer, Juergen O.
Metzger
- Title: Detection of Transient Radical Cations in Electron Transfer
Initiated Diels-Alder Reactions by Electrospray Ionization Mass
Spectrometry
- Date of Upload: 2004
- Article: J. AM. CHEM. SOC. 2004, 126, 14485-14492, Department of Pure and Applied Chemistry,
University of Oldenburg, Oldenburg, Germany
- Keywords: Cycloaddition, Mass spectrometry, Microreactor, Radical
cation, Reactive intermediate, ESI-MS, electrosprayionazation, mass
spectrometry, reaction, solution
- Abstract:
- Abstract:The coupling of a simple microreactor to an atmospheric pressure
ion source, such as electrospray ionization (ESI) or atmospheric pressure
chemical ionization (APCI), allows the investigation of reactions in solution
by mass spectrometry. The tris( p-bromophenyl)aminium hexachloroantimonate
(1.+SbCl6- )- initiated reactions of phenylvinylsulfide
(2) and cyclopentadiene (3) and of trans-anethole
(5) and isoprene (6) and the dimerization
of 1,3-cyclohexadiene (8) to give the respective Diels-Alder
products were studied. These preparatively interesting reactions proceed as
radical cation chain reactions via the transient radical cations of the respective
dienophiles and of the respective Diels-Alder addition products. These radical
cations could be detected directly and characterized unambiguously in the
reacting solution by ESI-MSMS. The identity was confirmed by comparison with
MS-MS spectra of the authentic radical cations obtained by APCI-MS and by
CID experiments of the corresponding molecular ions generated by EI-MS. In
addition, substrates and products could be monitored easily in the reacting
solution by APCI-MS.
- URL: http://www.chemie.uni-oldenburg.de/oc/metzger/publikationen/pdf/105.pdf
(application/pdf)
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