ozonides

Ozonides are chemical compounds that contain the ozonide functional unit O3− or, in organic chemistry, structures formed during ozonolysis of alkenes. In inorganic chemistry, ozonides are salts of the ozonide anion, typically pairing O3− with alkali or alkaline earth metals. Common examples are sodium ozonide (NaO3) and potassium ozonide (KO3). These inorganic ozonides are highly reactive oxidants, usually moisture sensitive, and are prepared by reactions involving ozone and metal reagents under controlled, low-temperature conditions.

Organic ozonides arise during the ozonolysis of carbon–carbon double bonds. The reaction first forms a primary ozonide (the molozonide), which rapidly rearranges to a more stable secondary ozonide, a cyclic 1,2,3-trioxolane. Secondary ozonides can be isolated in some cases, but more often they are subjected to a workup to yield carbonyl compounds. Reductive workups (for example, with zinc or dimethyl sulfide) typically furnish aldehydes and ketones, while oxidative workups can lead to carboxylic acids or other oxidized products, depending on substituents and conditions.

Properties and hazards vary by class. Inorganic ozonides are powerful oxidants and can be explosive or decomposed by moisture, light, or heat. Organic ozonides are useful intermediates in synthetic routes but are generally reactive and must be handled with care due to their instabilities and potential hazards.

See also: ozonolysis, ozonide chemistry, oxidative and reductive workups of ozonides.