23253-30-7

Basic information

• Product Name: 3-Phenyl-1,2,4-trioxolane
• Synonyms: 3-Phenyl-1,2,4-trioxolane;Ethenyl benzene ozonide
• CAS NO: 23253-30-7
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• Mol File: 23253-30-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Phenyl-1,2,4-trioxolane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Phenyl-1,2,4-trioxolane(23253-30-7)
• EPA Substance Registry System: 3-Phenyl-1,2,4-trioxolane(23253-30-7)

Safety Data

• Hazardous Substances Data: 23253-30-7(Hazardous Substances Data)

Upstream product

• 100-42-5 styrene 
• 107-31-3 Methyl formate 
• 79-20-9 acetic acid methyl ester 
• 70742-10-8 Styrolozonid 
• 100-52-7 benzaldehyde 
• 16609-27-1 4-Methylendispiro<2.1.2.2>nonan 
• 141-78-6 ethyl acetate 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 249894-61-9 3-Phenyl-1,2,4-trioxaspiro[5.4]decane 

Relevant articles and documents

Kinetics of Ozonation. 1. Electron-Deficient Alkenes

Absolute rate of reaction of ozone with a series of alkenes bearing electron-withdrawing groups have been determined at several temperatures in CCl4 by a stopped-flow technique.From these data, activation parameters have been calculated and range from tho

Highly efficient biphasic ozonolysis of alkenes using a high-throughput film-shear flow reactor

A new method for ozonolysis of alkenes using a continuous flow film-shear reactor was developed. The reactor uses a shearing microfluidic mixing chamber to provide biphasic mixing of an organic phase and aqueous phase with ozone gas. The H2O acts as an in situ reducing agent for the carbonyl oxide intermediate, providing ketones and aldehydes directly from the reaction mixture. Flow rates of up to 1.0 mmol/min (alkene) with an ozone reaction efficiency of >70% were achieved. Aryl conjugated olefins reacted to form carbonyl species in good yields on a multi-gram scale; however, alkyl olefins reacted with ozone to predominantly form secondary ozonides. The discrepancy in product distributions between alkyl and aryl olefins likely originates from the electronic stability of the carbonyl oxide intermediate, which is longer lived for aryl derivatives due to conjugation.

'Reductive ozonolysis' via a new fragmentation of carbonyl oxides

This account describes the development of methodologies for 'reductive' ozonolysis, the direct ozonolytic conversion of alkenes into carbonyl groups without the intermediacy of 1,2,4-trioxolanes (ozonides). Ozonolysis of alkenes in the presence of DMSO produces a mixture of aldehyde and ozonide. The combination of DMSO and Et3N results in improved yields of carbonyls but still leaves unacceptable levels of residual ozonides; similar results are obtained using secondary or tertiary amines in the absence of DMSO. The influence of amines is believed to result from conversion to the corresponding N-oxides; ozonolysis in the presence of amine N-oxides efficiently suppresses ozonide formation, generating high yields of aldehydes. The reactions with amine oxides are hypothesized to involve an unprecedented trapping of carbonyl oxides to generate a zwitterionic adduct, which fragments to produce the desired carbonyl group, an amine, and 1O2.

Selectivity in Lewis acid-mediated fragmentations of peroxides and ozonides: Application to the synthesis of alkenes, homoallyl ethers, and 1,2-dioxolanes

Fragmentation of dialkyl peroxides and ozonides is strongly influenced by the choice of Lewis acid. TiCl4 promotes C-O ionization (SN1 reaction) of tertiary peroxides while SnCl4 and BF3·OEt2 promote O-O heterolysis (Hock reaction). The cationic intermediates are trapped with allyltrimethylsilane to afford allylated alkanes and homoallyl ethers. In the absence of a nucleophile, ozonides (1,2,4-trioxolanes) invariably undergo O-O heterolysis. However, the combination of allyltrimethylsilane and SnCl4 results in formation of 1,2-dioxolanes via trapping of intermediates derived from SN1 ionization.

SnCl4-mediated reaction of ozonides with allyltrimethylsilane: Formation of 1,2-dioxolanes

SnC14-mediated reaction of ozonides (1,2,4-trioxolanes) with allyltrimethylsilane furnishes trimethylsilylmethyl-1,2-dioxolanes via metalated carbonyl oxides. The carbonyl oxides can arise through initial ionization of either the ether or peroxide oxygens.

Ozonolysis of styrene

Ozonolysis of styrene was studied. The effect of solvent and active additive on the yield of final products was examined. 1999 MAHK "Hayka/Interperiodica".

Synthesis of 1,2-Dioxolanes by Ozonolysis of 1,1-Disubstituted Nonactivated Olefins

Ozonolyses of the cyclopropyl-substituted olefins 2a, 2b, and 2c do not produce the carbonyl oxides 1a, 1b, and 1c but formaldehyde oxide (1d); 1d can be trapped by the starting olefin and provides the 1,2-dioxolanes 6a, 6b, and 6c, respectively, in ca. 10percent yield.Other dioxolanes and normal ozonides may be obtained by the addition of olefins or aldehydes to solutions of the primary ozonides of 2a and 2b.Key-Words: Ozonolysis / Alkylidenecycloalkanes / Carbonyl oxides / 1,2-Dioxolanes / 1,2,4-Trioxolanes

Crossed Ozonide Formation in the Ozonolysis of Styrene

Styrene-benzaldehyde mixtures (unsubstituted and the p-nitro, p-chloro, and p-methyl systems) were ozonized in CDCl3 at 0 deg C.The yields of styrene ozonide and of the two crossed ozonides (stilbene and ethylene ozonides) were determined.The cleavage dir

OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XVIII. INVESTIGATION OF A NEW OZONOLYTIC SYNTHESIS OF CARBOXYLIC ACIDS

By identification of the 18O isotope label in the oligomeric peroxide obtained by ozonization of a cyclic olefin in the presence of heavy oxygen and also in the product from catalytic isomerization of this peroxide ( the α,ο-dicarboxylic acids or its dimethyl ester ) it was shown that oxygen enters the ozonolysis product when the reaction is carried out in ether solvents.It is suggested that the increased content of active oxygen in the ozonolysis peroxy product is due to oxidation of the ether solvent to form α-hydroperoxide and addition of the latter to the oligomeric zwitterion, solvated by the polar solvents.It was established that the catalytic and thermal isomerization of the oligomeric peroxides and ozonides of cyclic olefins to the α,ο-dicarboxylic acids and ο-formyl carboxylic acids occurs through the oligomeric α-hydroxy peresters and α-hydroxy esters respectively.