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

César Márquez | Zendy; Haoyang Wang | Zendy; Francesco Fabbretti | Zendy; Jürgen O. Metzger | Zendy

Open Access

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

Author(s) -

César Márquez,

Haoyang Wang,

Francesco Fabbretti,

Jürgen O. Metzger

Publication year - 2008

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja806791c

Subject(s) - chemistry , mass spectrometry , radical ion , electrospray ionization , photochemistry , microreactor , cyclobutane , catalysis , electron transfer , organic chemistry , ion , chromatography , ring (chemistry)

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.

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