Dioxirane
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| Names | |||
|---|---|---|---|
| IUPAC name
Dioxirane | |||
| Identifiers | |||
157-26-6  | |||
| ChemSpider | 396025  | ||
| Jmol interactive 3D | Image | ||
| PubChem | 449520 | ||
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| Properties | |||
| CH2O2 | |||
| Molar mass | 46.03 g/mol | ||
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
| verify (what is ?) | |||
| Infobox references | |||
In chemistry dioxirane is a heterocyclic compound composed of one carbon and two oxygen atoms; it may be thought of as the smallest cyclic organic peroxide. The compound is highly unstable and has never been isolated at room temperature. Compounds containing dioxirane as a functional group, called dioxiranes, often possess better stability and are used in organic synthesis as oxidizing reagents,[1] most notably in the Shi epoxidation reaction. A relatively stable dioxirane in common use is dimethyldioxirane (DMDO) which is derived from acetone.
Synthesis
Dioxirane is highly unstable and the majority of studies of it have been computational; it has been detected during the low temperature (-196°C) reaction of ethylene and ozone,[2] although even at these temperatures such a mixture can be explosive.[3] Its formation is thought to be radical in nature, preceding via a Criegee intermediate. Microwave analysis has indicated C-H, C-O and O-O bond lengths of 1.090, 1.388 and 1.516 Å respectively.[3] The very long and weak O-O bond (c.f. hydrogen peroxide O-O = 1.47 Å) is the origin of its instability.
See also
References
- ↑ Ruggero Curci, Anna Dinoi, and Maria F. Rubino (1995). "Dioxirane oxidations: Taming the reactivity-selectivity principle" (PDF). Pure & Appl. Chem. 67 (5): 811–822. doi:10.1351/pac199567050811.
- ↑ Lovas, F.J.; Suenram, R.D. (November 1977). "Identification of dioxirane (H2) in ozone-olefin reactions via microwave spectroscopy". Chemical Physics Letters 51 (3): 453–456. doi:10.1016/0009-2614(77)85398-0.
- 1 2 Suenram, R. D.; Lovas, F. J. (August 1978). "Dioxirane. Its synthesis, microwave spectrum, structure, and dipole moment". Journal of the American Chemical Society 100 (16): 5117–5122. doi:10.1021/ja00484a034.