Dioxirane

Not to be confused with Dioxane.

Dioxirane

80px 100px
120px
Names
IUPAC name Dioxirane
Identifiers
CAS Number	157-26-6 Y
ChemSpider	396025 N
Jmol 3D model	Interactive image
PubChem	449520
InChI InChI=1S/CH2O2/c1-2-3-1/h1H2 N Key: ASQQEOXYFGEFKQ-UHFFFAOYSA-N N InChI=1/CH2O2/c1-2-3-1/h1H2 Key: ASQQEOXYFGEFKQ-UHFFFAOYAK
SMILES C1OO1
Properties
Chemical formula	CH2O2
Molar mass	46.03 g/mol
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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, 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, although even at these temperatures such a mixture can be explosive. 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. 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

• Oxaziridine
• Ethylene oxide
• 1,2-Dioxetane
• 1,3-Dioxetane