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Dimesityldioxirane

From Wikipedia, the free encyclopedia
Dimesityldioxirane
Names
IUPAC name
3,3-bis(2,4,6-trimethylphenyl)dioxirane
Identifiers
3D model (JSmol)
ChemSpider
  • 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
  • CC1=CC(=C(C(=C1)C)C2(OO2)C3=C(C=C(C=C3C)C)C)C
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).

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

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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

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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

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References

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  1. ^ 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.
  2. ^ 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.
  3. ^ Walton, Lesley (1996-01-01). Epoxidation using dioxiranes (PhD thesis). Loughborough University.