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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Singlet-oxygen generation in the catalytic reaction of dioxiranes with nucleophilic anions
Waldemar Adam1, Dmitri V Kazakov, Valeri P Kazakov
1Institut für Organische Chemie der Universität Würzburg, Am Hubland, Würzburg, Germany. adam@chemie.uni-wuerzburg.de
Abstract:
Nucleophilic anions such as Cl(-), I(-), Br(-), t-BuO(-), O(2)(-) and OH(-) efficiently catalyze the decomposition of dimethyldioxirane (DMD) and methyl(trifluoromethyl)dioxirane (TFD). Singlet oxygen ((1)O(2)) is formed in these catalytic reactions, as demonstrated by the characteristic infrared chemiluminescence (IR-CL) at 1268 nm. The yield of (1)O(2) 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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