Electron-Transfer-Catalyzed Dimerization of trans-Anethole: Detection of the Distonic Tetramethylene Radical Cation Intermediate by Extractive Electrospray Ionization Mass Spectrometry

The desolvating droplets of EESI were used as microreactor for the mass spectrometric study of short-lived transients of reactions in condensed liquid phase in the millisecond time region. The electron-transfer-catalyzed dimerization of trans-anethole was investigated and the intermediates in the ra...

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Published inJournal of the American Chemical Society Vol. 130; no. 51; pp. 17208 - 17209
Main Authors Marquez, Cesar A, Wang, Haoyang, Fabbretti, Francesco, Metzger, Jürgen O
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 24.12.2008
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Summary:The desolvating droplets of EESI were used as microreactor for the mass spectrometric study of short-lived transients of reactions in condensed liquid phase in the millisecond time region. The electron-transfer-catalyzed dimerization of trans-anethole was investigated and the intermediates in the radical cation chain reaction were isolated and characterized by MS−MS. The distonic tetramethylene radical cation 3 o •+ was detected as intermediate, and its cyclization to give the cyclobutane radical cation 3 c •+ was observed giving strong evidence that the reaction takes place stepwise.
Bibliography:Additional ESI-MS−MS and EESI-MS−MS spectra. This material is available free of charge via the Internet at http://pubs.acs.org.
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content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja806791c