Triozonides

Benzoyl azide Biphenyl triozonide Boron tribromide Bromine azide Bromine solutions... 

Benzene Triozonide (Ozobenzene, Benzoltriozonid in Ger). CjjH CU (probable structure given by Beilstein, Ref 1) white, amorph, si volatile solid sol in benz, insol in ale, eth, chlf, CS2 and ligroin. Prepd by Renard (Ref 2) and Harries et al (Refs 3 4) by passing ozone thru pure benz (thiophene free), cooled to 5—10°... 

Urushioldimethylethertriozonide (Triozonid des Urushiol-dunethylathers in Ger). C22H3402(03)3, light-yel oily liq, explds on heating or on exposure to flame. Prepd by Majima (Ref 2) by passing 6% ozone thru a chloroform soln of dimethyl-urushiol, ice cooled, for 16 hours... 

With benzene and aromatic hydrocarbons in general On particular phenylamine), the triozonide formed is insoluble and forms a very unstable gel. There was a violent detonation during the ozonisation of rubber dissolved in benzene. A gelatinous precipitate formed just before the detonation of this reaction. 

With ozone, phenylamine forms a triozonide, which separates in the form of a gelatinous mass that is extremely unstable. 

Ozonolysis was once used to locate the position of a double bond (or bonds) in unsaturated compounds of unknown structure—largely because of the ease of characterisation of the carbonyl products— but has now been superseded by physical methods, e.g. n.m.r. spectroscopy, which are easier and quicker. Benzene forms a triozonide which decomposes to yield three molecules of glyoxal, OHC—CHO the sole reaction of benzene that suggests it may contain three real double bonds in a Kekule structure Alkynes also undergo ozonolysis, but at a much slower rate than alkenes. 

During ozonisation of rubber dissolved in benzene, an explosion occurred. This seems unlikely to have been owing to formation of benzene triozonide (which separates as a gelatinous precipitate after prolonged ozonisation), since the solution remained clear. A rubber ozonide may have been involved, but the benzene-oxygen system itself has high potential for hazard. 

When dealing with ozonides always wear goggles, since ozonides, in particular amongst compounds of low molecular weight, are often explosive. Benzene triozonide, for example, is very dangerous. 

Benzene triozonide, 2343 trans-2-Butene ozonide, 1623 f 1,1-Dichloroethylene, Ozone, 0695... 

Benzene Triozonide, formerly known as Ozo-benz-ene (called Benzol triozonid in Ger), Ogs... 

Benzoic acid and other aromatic substs add on a molecule of ozone(03) at each of the double bonds of the benz nucleous to form triozonides. These compds are wh camphor-like substs at low temps and oils at RT. They are very unstable and tend to dec with expl violence at RT. In water they dec to form, probably, 1 mol of oxygen, 2 mols glyoxal, 1 mol formic acid, and 1 mol of a dibasic acid... 

Benzoic acid triozonide was prepd by treating the acid in chlf and CC14 at 0-15° with ozone for 20 hrs. One sample of the triozonide exploded in a desiccator. This triozonide was less stable than that of either benzylic acid, CgHg.CH2.CO-OH or of phenethylic(phenyl-(3-ethyl) acid, Cgf -CHj.CHj.COOH, which were obtd in lower yields Refs l)Beil- not found 2)H.Ruppe H.Hirsch-... 

This triozonide, prepared from phosphorus trioxide, decomposes from 35°C in solution evolving oxygen. The solid, isolable at —78°C, tends to explode on heating. 

Oxynitrotriazole, see 3-Nitro-l,2,4-triazolone, 0712 Ozobenzene, see Benzene triozonide, 2336... 

Allyl trimethylsilane can be used to displace the reactive chlorine atom in ozonide 70 and further treatment with ozone gives a diozonide. Similarly, a triozonide can be obtained from the corresponding 2,4-bis-allyl ozonide <2004EJO3657>. 

---