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Singlet-oxygen generation in the catalytic reaction of dioxiranes with nucleophilic anions

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Abstract

Nucleophilic anions such as Cl−, I−, Br−, t-BuO−, O2− and OH− efficiently catalyze the decomposition of dimethyldioxirane (DMD) and methyl(trifluoromethyl)dioxirane (TFD). Singlet oxygen (1O2) is formed in these catalytic reactions, as demonstrated by the characteristic infrared chemiluminescence (IR-CL) at 1268 nm. The yield of 1O2 generation, measured by the IR-CL method, lies in the range between 2 and 98%, which depends on the particular anion employed. For the bromide ion, the catalytic decomposition of the dioxirane is in competition with the oxidation of Br− to elemental bromine.

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Authors and Affiliations

  1. Institut für Organische Chemie der Universität Würzburg, Am Hubland, D-97074, Würzburg, Germany

    Waldemar Adam & Dmitri V. Kazakov

  2. Institut für Physikalische Chemie der Universität Würzburg, Am Hubland, D-97074, Würzburg, Germany

    Wolfgang Kiefer & Sebastian Schlücker

  3. Institute of Organic Chemistry, Ufa Scientific Center of the RAS, 71 Prospect Oktyabrya, 450054, Ufa, Russia

    Dmitri V. Kazakov, Valeri P. Kazakov & Ramilya R. Latypova

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  1. Waldemar Adam
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  2. Dmitri V. Kazakov
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  3. Valeri P. Kazakov
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  4. Wolfgang Kiefer
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  5. Ramilya R. Latypova
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  6. Sebastian Schlücker
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Correspondence to Dmitri V. Kazakov.

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Adam, W., Kazakov, D.V., Kazakov, V.P. et al. Singlet-oxygen generation in the catalytic reaction of dioxiranes with nucleophilic anions. Photochem Photobiol Sci 3, 182–188 (2004). https://doi.org/10.1039/b311009p

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