Sven Fuermeyer et.al.: Use of electrospray ionization mass spectrometry for
the investigation of radical cation chain reactions in solution: detection of
transient radical cations
- Author(s): Sven Meyer, Juergen O. Metzger
- Title: Use of electrospray ionization mass spectrometry for the investigation
of radical cation chain reactions in solution: detection of transient radical
cations
- Date of Upload: 2003
- Article: Anal Bioanal Chem (2003) 377 : 1108–1114, Department of Chemistry,
University of Oldenburg, Carl-von-Ossietzky-Str. 9-11, 26129 Oldenburg, Germany
- Keywords: Cycloaddition, Mass spectrometry, Microreactor, Radical
cation, Reactive intermediate, ESI-MS, electrosprayionazation, mass spectrometry,
reaction, solution
- Abstract:
- Electrospray ionization mass spectrometry (ESI-MS) coupled to a microreactor
is an excellent tool for the investigation of reactions in solution. Here,
we report the first results of our investigations into preparatively interesting
electron-transfer-initiated chain reactions in solution which proceed via
radical cations as reactive intermediates. The tris(p-bromophenyl)aminium
hexachloroantimonate (1)-mediated [2+2] cycloaddition of trans-anethole (2)
to give 1,2-bis(4-methoxyphenyl)-3,4-dimethylcyclobutane (3) was investigated.
The reaction proceeds as a radical cation chain reaction via transient intermediates
2•+ and 3•+ that could be detected and
characterized unambiguously directly in the reacting solution by ESI-MS/ MS.
The identity of the intermediates was confirmed by comparison with authentic
MS/MS spectra of 2•+ and 3•+ obtained by atmospheric
pressure chemical ionization mass spectrometry (APCI-MS). In addition, substrate
and product can be monitored easily in the reacting solution by APCI-MS.
- URL: http://www.chemie.uni-oldenburg.de/oc/metzger/publikationen/pdf/98.pdf
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