Dimesityldioxirane is a substituted
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 ...
with two
mesityl groups attached to the dioxirane carbon. It is a colorless crystalline substance stable in its solid state around -20 °C.
Structure
The molecule possesses approximately
C2 symmetry and the mesityl groups are twisted by 54.2°. The bulky mesityl groups cause
steric strain Van der Waals strain is strain resulting from Van der Waals repulsion when two substituents in a molecule approach each other with a distance less than the sum of their Van der Waals radii.
Van der Waals strain is also called Van der Waals repul ...
which is reduced by increase in R
1–C–R
2 angle from 117° in dioxirane to 119.2° in dimesityldioxirane. The mesityl groups also rotate about the single bond, consequently reducing steric repulsions further.
Synthesis and Uses
Dimesityldioxirane was first isolated at room temperature in pure as well as in solution form in 1994.
It was synthesised by irradiation of its
diazo derivative in
trichlorofluoromethane
Trichlorofluoromethane, also called freon-11, CFC-11, or R-11, is a chlorofluorocarbon (CFC). It is a colorless, faintly ethereal, and sweetish-smelling liquid that boils around room temperature. CFC-11 is a Class 1 ozone-depleting substance w ...
at 183K to form , followed by oxidation. The synthesis had a yield of 50%.
It can mainly be used 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 ...
but is less oxidizing than other dioxiranes due to its stability.
See also
*
Difluorodioxirane
*
Dimethyldioxirane
Dimethyldioxirane (DMDO) is the organic compound with the formula . It is the dioxirane derived from acetone and can be viewed as the monomer of acetone peroxide. It is a powerful selective oxidizing agent that finds some use in organic synthesis ...
*
Shi epoxidation
References
{{reflist
Dioxiranes
Organic peroxides
Oxidizing agents