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 (application/pdf)


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