Sodium ozonide

The ozonides are characterized by the presence of the ozonide ion, O - They are generally produced by the reaction of the inorganic oxide and ozone (qv). Two reviews of ozonide chemistry are available (1,117). Sodium ozonide [12058-54-7] NaO potassium ozonide [12030-89-6] 35 rubidium ozonide [12060-04-7] RbO and cesium ozonide [12053-67-7] CsO, have all been reported (1). Ammonium ozonide [12161 -20-5] NH O, and tetramethylammonium ozonide [78657-29-1/, (CH ) NO, have been prepared at low temperatures (118). 

Sodium nitroprusside, 74 536 Sodium nonoxynol-25 sulfate cosmetic surfactant, 7 834t Sodium oleoyl isethionate cosmetic surfactant, 7 834t Sodium orthophosphates, 73 8321 Sodium orthosilicates commercial, 22 465, 466t, 469t manufacture of, 22 464, 465 Sodium oxide(s), 2 273, 22 765 in cement, 5 468 contamination by, 22 776 Sodium ozonide, 79 417 Sodium palmitate, as soap, 22 726 Sodium pentaborate... 

It was not possible to isolate this from liquid ammonia solution after formation by an exchange reaction with caesium ozonide. It was possible to isolate a cryptand complex, which was violently explosive but permitted diffraction studies. Sodium ozonide behaved similarly, though the other three alkali ozonides do not oxidise ammonia during isolation attempts. 

The deep red ozonide ion has a bent structure, and sodium ozonide is isostructural with sodium nitrite (NaNC>2). The X-ray structural data of the alkali metal ozonides show that an increase in cationic size corresponds to a decrease in 0-0 bond length and an increase in 0-0-0 angle, as summarized in the following table ... 

Palladium Arsenic, carbon, ozonides, sulfur, sodium tetrahydridoborate... 

The hydroperoxide (POOH) concentration was determined iodometri-cally after decomposition of the ozonides with excess of alcoholic sodium hydroxide. 

Palladium Paraformaldehyde Paraldehyde Pentaborane-9 Pentacarbonyliron Arsenic, carbon, ozonides, sulfur, sodium tetrahydridoborate Liquid oxygen Alkalies, HCN, iodides, nitric acid, oxidizers Dimethylsulfoxide Acetic acid, nitric oxide, transition metal halides, water, zinc... 

As already written earlier sodium borohydride in presence of BF3 can generate diborance in situ. The ozonides can be reduced to alcohols. 

Dichloroaluminium hydride in ether or sodium borohydride in TEA can lead to formation of ethers from ozonides by reductive cleavage of the two C—O bonds of the peroxide bridge (Equation (19)) <85JOC275>. 

Oxidative hydrolysis transforms the intermediate ozonide into ketone(s) and/or carboxylic acid(s) in good yields. H202 in water, in sodium hydroxide solution, or in formic acid is the best proven oxidant.582,584,592 Peroxy acids and silver oxide are also employed. Rearrangement and overoxidation may be undesirable side-reactions. A simple two-step ozonation in MeOH yields methyl esters without added oxidizing agent.627... 

Le Carrer-Le Goff and co-workers have reported an expeditious synthetic route to a-substituted statines by the well-defined metal-mediated allylation of V-protected a-amino aldehydes followed by the ozonolysis of the double bond (Scheme 11.3).16 Ozonolysis of the double bond in 13, carried out in dichloromethane/methanol, at -78°C in the presence of sodium hydroxide permits the intermediate ozonide to be converted directly to the statine methyl ester 14.17... 

Ozone reacts with a solution of sodium in liquid ammonia, yielding an orange to brown precipitate. The product is readily decomposed by water or dilute acids with evolution of oxygen. It is possibly an ozonide of sodium, but owing to interaction of the ozone and ammonia 7 it has not been found possible to isolate it in the pure state. Potassium, rubidium, and ejesium react similarly.8... 

The determination of the active oxygen in ozonides with sodium iodide in glacial acetic acid gives reliable values only in the case of ketozonides. The reaction products are ketones.96 Iodometric peroxide determination in the case of aldozonides gives less than 60% of the theoretical value 112 carboxylic acids are formed as well as aldehydes. The reduction with iodide ions probably suffers competition from the reaction shown in Eq. (7). 

Catalytic hydrogenation114-116 also leads to carbonyl compounds, acids being formed in a side reaction.110 Reduction of the ozonides with lithium aluminum hydride117 119 and with sodium borohydride119 yields alcohols. 

Sidewall-functionalized carbon nanotubes were prepared by Wong [4] using ozone with an oxygen carrier then postreacted with sodium hydride or DMS to decompose primary ozonides to form aldehydes and ketones. 

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