Difluorodioxirane (CF₂O₂) is a rare, stable member of the

dioxirane In chemistry, dioxirane (systematically named dioxacyclopropane, also known as methylene peroxide or peroxymethane) is an organic compound with formula . The molecule consists of a ring with one methylene and two oxygen atoms. It is of interes ...

family, known for a single oxygen-oxygen bond (O-O). Unlike most dioxiranes that decompose quickly, difluorodioxirane is surprisingly stable at room temperature, making it potentially useful for further research and applications.

Synthesis

Difluorodioxirane was first synthesised by Russo and DesMarteau in 1993 by treating fluorocarbonyl hypofluorite (FCOOF) with X₂ (= F2, Cl2 or ClF) over pelletized CsF in a flow system. It also likely exists as a possible intermediate in reactions involving other fluorine-containing compounds.

Properties

Unlike most dioxiranes that decompose quickly, difluorodioxirane is surprisingly stable at room temperature due to the stabilising interacton of two

fluorine Fluorine is a chemical element; it has Chemical symbol, symbol F and atomic number 9. It is the lightest halogen and exists at Standard temperature and pressure, standard conditions as pale yellow Diatomic molecule, diatomic gas. Fluorine is extre ...

atoms with the ring. This effect makes the O-O bond less reactive and more stable compared to other dioxiranes. The central F–C–F angle is 109°, approximately a tetrahedral angle. Difluorodioxirane is known for its ability to perform regiospecific and stereoselective oxidations. This makes it a valuable tool in organic synthesis for precise manipulation of molecules. Despite its increased stability, difluorodioxirane can still act as an

oxidizing agent An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or " accepts"/"receives" an electron from a (called the , , or ''electron donor''). In ot ...

, transferring

oxygen Oxygen is a chemical element; it has chemical symbol, symbol O and atomic number 8. It is a member of the chalcogen group (periodic table), group in the periodic table, a highly reactivity (chemistry), reactive nonmetal (chemistry), non ...

to other molecules. it often leads to cleaner and more predictable reaction outcomes due to its controlled reactivity.

Uses

Difluorodioxirane itself has not yet found widespread applications due to its recent discovery. However, its unique stability and reactivity similar to other dioxiranes suggest potential uses in several areas: *Organic synthesis: Due to its oxidizing properties, difluorodioxirane could be a valuable reagent in organic reactions, particularly for controlled oxidation processes. Researchers are exploring its potential applications in

epoxidation In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ...

(adding oxygen atoms to create

epoxide In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ...

rings),

hydroxylation In chemistry, hydroxylation refers to the installation of a hydroxyl group () into an organic compound. Hydroxylations generate alcohols and phenols, which are very common functional groups. Hydroxylation confers some degree of water-solubility ...

(adding

hydroxyl groups In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

-OH), and other oxidation reactions. *Development of new catalysts: The stability and reactivity profile of difluorodioxirane make it a promising candidate for the development of new and more efficient catalysts for various organic transformations.

References

{{reflist Dioxiranes Organic peroxides Oxidizing agents Heterocyclic compounds with 1 ring Oxygen heterocycles

Synthesis

Properties

Uses

See also

References