Formation of dioxirane from carbonyl oxide

Cremer, Dieter ; Schmidt, Thomas ; Gauss, Jürgen ; Radhakrishnan, T. P. (1988) Formation of dioxirane from carbonyl oxide Angewandte Chemie International Edition, 27 (3). pp. 427-428. ISSN 1433-7851

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1 H2C=O-O → O-^O 2The isomerization (a) should be exothermic and should have an activation barrier of 23 kcal mol-1. This follows from the results of ab initio calculations, which, moreover, suggest an initiating pyramidalization at the central O atom, which is facilitated by Π-donor substituents like fluorine: In cis- and trans-HFCO2 the activation energy is still only 17 and 8 kcal mol-1, respectively. However, fluorodixirane is kinetically less stable than 2. Only geminal methyl groups effect both a thermodynamic and a kinetic stabilization.

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