Dimesityldioxirane
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| IUPAC name
3,3-bis(2,4,6-trimethylphenyl)dioxirane
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| Properties | |
| 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).
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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]
Structure
[edit]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
[edit]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
[edit]References
[edit]- ^ a b Kirschfeld, Andreas; Muthusamy, Sengodagounder; Sander, Wolfram (1994-11-17). "Dimesityldioxirane—A Dioxirane Stable in the Solid State". Angewandte Chemie International Edition in English. 33 (21): 2212–2214. doi:10.1002/anie.199422121. ISSN 0570-0833.
- ^ Sander, Wolfram; Schroeder, Kerstin; Muthusamy, Sengodagounder; Kirschfeld, Andreas; Kappert, Wilhelm; Boese, Roland; Kraka, Elfi; Sosa, Carlos; Cremer, Dieter (1997-08-01). "Dimesityldioxirane". Journal of the American Chemical Society. 119 (31): 7265–7270. doi:10.1021/ja964280n. ISSN 0002-7863.
- ^ Walton, Lesley (1996-01-01). Epoxidation using dioxiranes (PhD thesis). Loughborough University.