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- Title
Use of electrospray ionization mass spectrometry for the investigation of radical cation chain reactions in solution: detection of transient radical cations.
- Authors
Meyer, Sven; Metzger, Jürgen O.
- 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&ding6C;+ and 3&ding6C;+ 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&ding6C;+ and 3&ding6C;+ 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.
- Subjects
ELECTROSPRAY ionization mass spectrometry; OXIDATION-reduction reaction; CHARGE exchange; CATIONS; CHEMICAL ionization mass spectrometry; SOLUTION (Chemistry)
- Publication
Analytical & Bioanalytical Chemistry, 2003, Vol 377, Issue 7/8, p1108
- ISSN
1618-2642
- Publication type
Article
- DOI
10.1007/s00216-003-2230-5