Dimethyldioxirane

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Dimethyldioxirane
Names
IUPAC name
3,3-Dimethyldioxirane
Other names
Dimethyl dioxirane
DMDO
Murray's reagent
Properties
C3H6O2
Molar mass 74.08 g/mol
Appearance Unknown in pure form
Odor Odorless
Melting point Unknown
Boiling point Unknown
Solubility Soluble in acetone
Hazards
Safety data sheet None
Related compounds
Related compounds
Acetone peroxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dimethyldioxirane (DMDO), also referred to as Murray's reagent, is a dioxirane derived from acetone and can be considered as a monomer of acetone peroxide. It is a powerful yet selective oxidizing agent which finds use in organic synthesis.

Properties

Chemical

DMDO can be used to oxidize alkenes to epoxides.

DMDO displays good selectivity for olefins. Typically, electron deficient olefins are oxidized more slowly than electron rich ones. DMDO will also oxidize several other functional groups. For example, DMDO will oxidize primary amines to nitro compounds and sulfides to sulfoxides.

In some cases, DMDO will even oxidize unactivated C-H bonds, such as those from tertiary carbons.

DMDO can also be used to convert nitro compounds to carbonyl compounds (Nef reaction).

Physical

Since the compound has not been isolated in pure form, its physical properties remain unknown so far.

Availability

DMDO is not commercially available because of its instability and has to be prepared in situ.

Preparation

DMDO can be prepared by the reaction of acetone with Oxone, where the potassium peroxymonosulfate is the active ingredient.[1]

The preparation of DMDO is rather inefficient (typical yields < 3%) and typically only yields a relatively dilute solution in acetone (only up to approximately 0.1 M).

Projects

  • Make epoxides
  • Make nitro compounds

Handling

Safety

DMDO is only stable in diluted solutions. It is a powerful oxidizer and will oxidize many organic compounds.

Storage

Solutions are stable under refrigeration (−10 to −20 °C) for up to a week. The rate of decomposition will increase upon exposure to light or heavy metals.

Disposal

Addition of a reducing agent will neutralize the compound.

References

  1. http://orgsyn.org/demo.aspx?prep=v90p0350

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