|Jmol-3D images||Image 1|
|Molar mass||74.08 g/mol|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Dimethyldioxirane (DMDO), also referred to as Murray's reagent, is a dioxirane derived from acetone. It is the most commonly used dioxirane in organic synthesis, and can be considered as a monomer of acetone peroxide.
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). However, this is of no consequence, since DMDO is prepared from extremely cheap starting materials: acetone, sodium bicarbonate, and potassium peroxymonosulfate (commercially known as "oxone"). The solution can be stored at low temperatures and assayed immediately prior to use to determine its actual concentration.
The most common use for DMDO is the oxidation of alkenes to epoxides. One particular advantage of using DMDO is that the only byproduct of oxidation is acetone, a fairly innocuous and volatile compound. DMDO oxidations are particularly mild, sometimes allowing oxidations which might not otherwise be possible. In fact, DMDO is considered the reagent of choice for epoxidation,[dubious ] and in nearly all circumstances is as good as or better than peroxyacids such as meta-chloroperoxybenzoic acid (mCPBA).
Despite its high reactivity, 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:
- Robert W. Murray and Megh Singh (1988), "Synthesis of epoxides using dimethyldioxirane]: trans-stilbene oxide", Org. Synth.; Coll. Vol. 9: 288