Dimesityldioxirane

Dimesityldioxirane is a substituted dioxirane with two mesityl groups attached to the dioxirane carbon. It is a colorless crystalline substance stable in its solid state around -20 °C.^[1]

Dimesityldioxirane

Names
IUPAC name 3,3-bis(2,4,6-trimethylphenyl)dioxirane
Identifiers
CAS Number	161807-01-8 N
3D model (JSmol)	Interactive image
ChemSpider	74833282
PubChem CID	86180054
InChI InChI=1S/C19H22O2/c1-11-7-13(3)17(14(4)8-11)19(20-21-19)18-15(5)9-12(2)10-16(18)6/h7-10H,1-6H3 Key: CIQXXABRSWBHGW-UHFFFAOYSA-N
SMILES CC1=CC(=C(C(=C1)C)C2(OO2)C3=C(C=C(C=C3C)C)C)C
Properties
Chemical formula	C19H22O2
Molar mass	282.4 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Structure

The molecule possesses approximately C₂ symmetry and the mesityl groups are twisted by 54.2°. The bulky mesityl groups cause steric strain which is reduced by increase in R₁–C–R₂ angle from 117° in dioxirane to 119.2° in dimesityldioxirane. The mesityl groups also rotate about the single bond, consequently reducing steric repulsions further.^[2]

Synthesis and Uses

Dimesityldioxirane was first isolated at room temperature in pure as well as in solution form in 1994.^[3] It was synthesised by irradiation of its diazo derivative in trichlorofluoromethane at 183K to form dimesitylcarbene, followed by oxidation. The synthesis had a yield of 50%.^[1]

It can mainly be used as an oxidizing agent but is less oxidizing than other dioxiranes due to its stability.

See also

• Difluorodioxirane
• Dimethyldioxirane
• Shi epoxidation