Intramolecular electron-transfer-induced cleavage of dioxetanes observed in fast-atom bombardment tandem mass spectrometry

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Eur. J. Mass Spectrom. 7, 441 - 445 (2001)

Intramolecular electron-transfer-induced cleavage of dioxetanes observed in fast-atom bombardment tandem mass spectrometry

Mamoru Ohashi,^* Masakazu Takanashi, Nobuko Watanabe and Masakatsu Matsumoto
Department of Chemistry, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa, Japan
Takumi Saisu and Haruki Niwa
Department of Applied Physics and Chemistry, The University of Electro-Communications, Chofu, Tokyo, Japan

ABSTRACT:

Phenolic spiroadamantyl-substituted dioxetanes are well known base-induced chemiluminescent compounds. Fast-atom bombardment collision-induced dissociation tandem mass spectrometry (FAB CID-MS/MS) of five phenolic spiroadamantyl-substituted dioxetanes in the negative-ion mode clearly showed that a highly efficient cleavage of the dioxetane rings took place to produce the corresponding phenolate ion almost exclusively. The mass spectrometric behavior of these compounds reflects the highly efficient intramolecular electron-transfer-induced cleavage of dioxetane rings, which participates in the highly efficient base-triggered chemiluminescent reactions of these compounds in solution.

Keywords: fast-atom bombardment, tandem mass spectrometry, 1,2-dioxetane, electron-transfer, admantanone, chemiluminescence

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