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Title: Dioxirane  
Author: World Heritage Encyclopedia
Language: English
Subject: Functional groups, Selenonic acid, Tellurol, Phosphonite, Heterocyclic compound
Publisher: World Heritage Encyclopedia


IUPAC name
ChemSpider  N
Jmol-3D images Image
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).
 N  (: YesY/N?)

In chemistry dioxirane is a [1] most notably in the Shi epoxidation reaction. A relatively stable dioxirane in common use is dimethyldioxirane (DMDO) which is derived from acetone.


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


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  3. ^ a b
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