23246-12-0

Basic information

• Product Name: 3,3,5-Triphenyl-1,2,4-trioxolane
• Synonyms: 3,3,5-Triphenyl-1,2,4-trioxolane;Triphenylethylene ozonide
• CAS NO: 23246-12-0
• Molecular Formula: C₂₀H₁₆O₃
• Molecular Weight: 0
• Mol File: 23246-12-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,3,5-Triphenyl-1,2,4-trioxolane(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3,5-Triphenyl-1,2,4-trioxolane(23246-12-0)
• EPA Substance Registry System: 3,3,5-Triphenyl-1,2,4-trioxolane(23246-12-0)

Safety Data

• Hazardous Substances Data: 23246-12-0(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 632-51-9 1,1,2,2-tetraphenylethylene 
• 58-72-0 Triphenylethylene 
• 5350-57-2 benzophenone hydrazone 
• 118017-04-2 diphenylcarbonyl oxide 
• 908093-98-1 diazodiphenylmethane 
• 4479-98-5 2,2,3-triphenyloxirane 

Downstream Products

• 93-58-3 benzoic acid methyl ester 
• 119-61-9 benzophenone 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 78485-09-3 3,3,5-Triphenyl-1,2-dioxacyclopentane 
• 82491-44-9 trans-3-Methyl-3-propyl-5-phenyl-1,2-dioxacyclopentane 
• 82491-43-8 cis-3-Methyl-3-propyl-5-phenyl-1,2-dioxacyclopentane 
• 79825-70-0 [²H₃]methyl benzoate 
• 86766-13-4 (3S,5R)-3-Heptyl-3-methyl-5-phenyl-[1,2]dioxolane 
• 86766-12-3 (3S,5S)-3-Heptyl-3-methyl-5-phenyl-[1,2]dioxolane 
• 86766-10-1 (3R,5R)-3-Ethyl-3,5-diphenyl-[1,2]dioxolane 
• 86766-09-8 (3R,5S)-3-Ethyl-3,5-diphenyl-[1,2]dioxolane 
• 86766-19-0 (3S,5R)-3-Isopropyl-3,5-diphenyl-[1,2]dioxolane 
• 86766-18-9 (3S,5S)-3-Isopropyl-3,5-diphenyl-[1,2]dioxolane 
• 86832-55-5 C₁₆H₁₅⁽²⁾HO₂ 

Relevant articles and documents

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.

Reactivity of aromatic compounds toward diphenylcarbonyl oxide

The reactivity of organic compounds (PhH, PhMe, PhF, PhCl, PhOH, PhOEt, PhCHO, Ph2CO, PhCN, Ph2S, Ph2SO, Ph2SO2, and p-Me2C6H4) toward diphenylcarbonyl oxide Ph2COO was characterized by the k33/k31 ratio, where k33 and k31 are the rate constants for the reactions of Ph2COO with the arene and diphenyldiazomethane Ph2CN2, respectively. The values of k33/k31, vary from 2.6 · 10-3 (PhCN) to 0.65 (Ph2S) (70 °C, MeCN). The reaction is preceded by formation of a complex with charge transfer from a substrate to Ph2COO. In the reactions with aromatic substances (except for Ph2SO, PhCHO, and Ph2CO), carbonyl oxide behaves as an electrophile.

Electronic Effects in the Reaction of Carbonyl Oxides with Aldehydes

Electronic effects in the third step of the Criegee mechanism of ozonolysis, i.e., the reaction of a carbonyl oxide with a carbonyl compound, were studied by using a non-ozone source of carbonyl oxides as well as by an ozonolysis method.Benzophenone oxide

THE PHOTOCHEMICAL PREPARATION OF OZONIDES BY ELECTRON-TRANSFER PHOTO-OXYGENATION OF EPOXIDES

9,10-Dicyanoanthracene (DCA) sensitizes the electron-transfer photo-oxygenation of epoxides in oxygen-saturated acetonitrile to form ozonides.Epoxides with oxidation potentials lower than 2 V vs SCE quench the fluorescence of DCA and are converted to the