Ozonides


Addition compounds called ozonides are produced when alkenes react with ozone and reductive cleavage of these compounds is used extensively in preparative and diagnostic organic chemistry.  [c.264]

How would you obtain a sample of pure ozone Account for the conditions used in your method of preparation. What is the arrangement of oxygen atoms in an ozonide and what evidence would you cite in support of the structure you suggest  [c.308]

Oleic acid ozonide  [c.892]

Alkene Ozone Ozonide  [c.263]

Ozonides undergo hydrolysis in water giving carbonyl compounds  [c.263]

This cleavage reaction is more often seen in structural analysis than in synthesis The substitution pattern around a dou ble bond is revealed by identifying the carbonyl containing compounds that make up the product Hydrolysis of the ozonide intermediate in the presence of zinc (reductive workup) permits aide hyde products to be isolated without further oxidation  [c.710]

Palladium Arsenic, carbon, ozonides, sulfur, sodium tetrahydridoborate  [c.1210]

A 38.63-mg sample of potassium ozonide, KO3, was heated to 70 °C for 1 h, undergoing a weight loss of 7.10 mg. Write a balanced chemical reaction describing this decomposition reaction. A 29.6-mg sample of impure KO3 experiences a 4.86-mg weight loss when treated under similar condition. What is the %w/w KO3 in the sample  [c.269]

Secondary ozonide Secondary plasticizer Secondary recycling Secondary structures Secosteroid  [c.875]

The relevant properties of peroxide and superoxide salts are given in Table 4 (see Peroxides and peroxide compounds, inorganic). Potassium peroxide is difficult to prepare and lithium superoxide is very unstable. The ozonides, MO3, of the alkah metals contain a very high percentage of oxygen, but are only stable below room temperature (see Ozone).  [c.486]

Oxygen Compounds. Although hydrogen peroxide is unreactive toward ozone at room temperature, hydroperoxyl ion reacts rapidly (39). The ozonide ion, after protonation, decomposes to hydroxyl radicals and oxygen. Hydroxyl ions react at a moderate rate with ozone (k = 70).  [c.492]

Formation of Ozonides. Although the patent compound, HO3, is too unstable to be isolated, metal and nonmetal ozonides have been  [c.492]

The stability of the alkali metal ozonides increases from Li to Cs alkaline-earth ozonides exhibit a similar stability pattern. Reaction of metal ozonides with water proceeds through the intermediate formation of hydroxyl radicals.  [c.492]

AH of the commercial inorganic peroxo compounds except hydrogen peroxide are described herein, as are those commercial organic oxidation reactions that are beheved to proceed via inorganic peroxo intermediates. Ozonides and superoxides are also included, but not the dioxygen complexes of the transition metals.  [c.90]

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).  [c.98]

The potassium salt is the best characterized. It is an orange-red paramagnetic soHd having a magnetic moment of 1.6 x 10 J/T (1.73 Xg). It reacts with water, yielding oxygen gas and potassium hydroxide. It decomposes to the superoxide, KO2, upon standing at room temperature. Potassium ozonide is prepared by ozonation of dry potassium hydroxide. It can be purified by extraction and recrystaUization from Hquid ammonia. Whereas the inorganic ozonides are of potential importance as soHd-oxygen carriers ia breathing apparatus, they are not produced commercially.  [c.98]

For the determination of the structure of unsaturated compounds, oxidation with ozone (as ozonised oxygen) possesses many advantages. Ozonolysis, unlike oxidation with excess of permanganate or chromic acid which, for example, will also oxidise primary and secondary alcohols, is a highly specific process. By passing ozonised oxygen through a solution of an ethylenio compound in an inert solvent, preferably at a low temperature, ozone adds on readily and quantitatively to the double bond to give an ozonide (I)  [c.888]

Excess of ozone should be avoided since further oxidation may occur to oxozonides or perozonides. ) The ozonides are usually not isolated since they are generally viscid oils or glasses, sometimes with violently explosive properties particularly on warming. They can, however, be completely  [c.888]

The general method of ozonisation consists in passing dry ozonised oxygen through a dilute solution of the ethylenic compound In a solvent such as ethyl acetate, glacial acetic acid, chloroform, carbon tetrachloride, hexane or ethyl chloride, cooled in a freezing mixture (preferably at —20° to —30°). A wash bottle charged with potassium Iodide solution and boric acid is attached to the outlet tube of the bottle containing the solution of the substance the completion of the ozonisation is indicated by a sudden extensive separation of iodine. The following procedures may be used for decomposing the resulting ozonides —  [c.889]

Organic peroxides are highly explosive, hence it is best to carry out the ozonisation in a solvent which dissolves both the original compound and the ozonide.  [c.891]

Dissolve 8 -2 g. of cyclohexene (Section 111,12) in 200 ml. of pure dry ethyl acetate (Section II,47,2S) contained in a 500 ml. glass-stoppered wash bottle, cool the solution to —20° to —30° or below (e.y., with solid carbon dioxide - acetone) and attach the wash bottle through a calcium chloride or cotton wool drying tube to another containing acidified potassium iodide solution. Pass ozonised oxygen until the reaction is complete, i.e., until iodine is abundantly liberated. Then add 0 5 g. of palladium - calcium carbonate catalyst, and hydrogenate the cold solution of the ozonide in the usual manner (compare Fig. Ill, 150, 1) cool the hydrogenation vessel in ice. FUter off the catalyst, remove the solvent (Fig. II, 13, 4 but with a Claisen flask provided with a fractionating side arm) at normal pressure. Distil the residue under reduced pressure and collect the adipic dialdehyde at 92-94°/12 mm. The yield is 7 g. This aldehyde oxidises readily and should be kept in a sealed tube in an atmosphere of nitrogen or carbon dioxide. It may be converted into the dioxime by warming with aqueous hydroxylamine acetate solution after. recrystaUisation from water, the dioxime has m.p. 172°.  [c.892]

The most common procedure is ozonolysis at -78 C (P.S. Bailey, 1978) in methanol or methylene chloride in the presence of dimethyl sulfide or pyridine, which reduce the intermediate ozonides to aldehydes. Unsubstituted cyclohexene derivatives give 1,6-dialdehydes, enol ethers or esters yield carboxylic acid derivatives. Oxygen-substituted C—C bonds in cyclohexene derivatives, which may also be obtained by Birch reduction of alkoxyarenes (see p. 103f.), are often more rapidly oxidized than non-substituted bonds (E.J. Corey, 1968 D G. Stork, 1968 A,B). Catechol derivatives may also be directly cleaved to afford conjugated hexa-dienedioic acid derivatives (R.B. Woodward, 1963), Highly regioselective cleavage of the more electron-rich double bond is achieved in the ozonization of dienes (W. KnOll, 1975),  [c.87]

Aldehydes are easily oxidized to carboxylic acids under conditions of ozonide hydroly SIS When one wishes to isolate the aldehyde itself a reducing agent such as zinc is included during the hydrolysis step Zinc reduces the ozonide and reacts with any oxi dants present (excess ozone and hydrogen peroxide) to prevent them from oxidizing any aldehyde formed An alternative more modem technique follows ozone treatment of the alkene m methanol with reduction by dimethyl sulfide (CH3SCH3)  [c.263]

The unstable ammonium ozonide [12161 -20-5] NH O, prepared at low temperatures by reaction of ozone withHquid ammonia, decomposes rapidly at room temperature to NH NO, oxygen, and water (51). Tetrametbylammonium ozonide [78657-29-1] also has been prepared.  [c.493]

Ozonation ofAlkenes. The most common ozone reaction involves the cleavage of olefinic carbon—carbon double bonds. Electrophilic attack by ozone on carbon—carbon double bonds is concerted and stereospecific (54). The modified three-step Criegee mechanism involves a 1,3-dipolar cycloaddition of ozone to an olefinic double bond via a transitory TT-complex (3) to form an initial unstable ozonide, a 1,2,3-trioxolane or molozonide (4), where R is hydrogen or alkyl. The molozonide rearranges via a 1,3-cycloreversion to a carbonyl fragment (5) and a peroxidic dipolar ion or zwitterion (6).  [c.493]

The dipolar ion can react in several ways according to the solvent and the stmcture of the olefin. In inert solvents, if the carbonyl compound is highly reactive (eg, an aldehyde), the dipolar ion can be added to the carbonyl fragment to give the normal ozonide or 1,2,4-trioxolane (7) for example, 1,1-and 1,2-dialkylethylenes react in this manner. Tri- or tetraalkyl-substituted olefins produce a smaH, if any, yield of an ozonide when the ozonolysis is  [c.493]

Commercially, pure ozonides generally are not isolated or handled because of the explosive nature of lower molecular weight species. Ozonides can be hydrolyzed or reduced (eg, by Zn/CH COOH) to aldehydes and/or ketones. Hydrolysis of the cycHc bisperoxide (8) gives similar products. Catalytic (Pt/excess H2) or hydride (eg, LiAlH reduction of (7) provides alcohols. Oxidation (O2, H2O2, peracids) leads to ketones and/or carboxyUc acids. Ozonides also can be catalyticaHy converted to amines by NH and H2. Reaction with an alcohol and anhydrous HCl gives carboxyUc esters.  [c.494]

Organic peroxides can be classified according to peroxide stmcture. There are seven principal classes hydroperoxides dialkyl peroxides a-oxygen substitued alkyl hydroperoxides and dialkyl peroxides primary and secondary ozonides peroxyacids diacyl peroxides (acyl and organosulfonyl peroxides) and alkyl peroxyesters (peroxycarboxylates, peroxysulfonates, and peroxyphosphates).  [c.101]


See pages that mention the term Ozonides : [c.294]    [c.294]    [c.294]    [c.294]    [c.889]    [c.889]    [c.889]    [c.889]    [c.892]    [c.263]    [c.263]    [c.217]    [c.186]    [c.805]    [c.908]    [c.976]    [c.492]    [c.494]    [c.98]    [c.117]   
Modern inorganic chemistry (1975) -- [ c.264 ]

Textbook on organic chemistry (1974) -- [ c.888 ]

Chemistry of the elements (1998) -- [ c.610 , c.611 ]

Hydrogenation methods (1985) -- [ c.176 ]