29833-83-8

Upstream product

• 101-02-0 triphenyl phosphite 

Downstream Products

• 115-86-6 phosphoric acid triphenyl ester 
• 841-46-3 ethyl diphenyl phosphate 
• 345304-95-2 6-(1-hydroperoxy-1-methyl)ethyl-2,2-dimethyl-1,3-dioxin-4-one 
• 345305-02-4 6-(1-(diphenylphosphoryl)peroxy-1-methyl)ethyl-2,2-dimethyl-1,3-dioxin-4-one 
• 107394-70-7 2,4,6-tri-tert-butylphenylphosphinic acid 
• 1121-37-5 dicyclopropyl ketone 
• 1489-69-6 Cyclopropanecarboxaldehyde 
• 32287-37-9 5,6,11,12-tetraphenyl-5,12-dihydro-5,12-epidioxido-naphthacene 
• 512-56-1 trimethyl phosphite 
• 10113-28-7 dimethyl phenyl phosphate 
• 115-89-9 phosphoric acid methyl ester diphenyl ester 

Relevant academic research and scientific papers

Substituent effects on the decomposition of chemiluminescent tricyclic aromatic dioxetanes

Three tricyclic 1,2-dioxetane derivatives, 1a, 2a and 3a were synthesized from their corresponding 1,4-dioxin acenaphthylene compounds, 1, 2 and 3, by reaction with singlet-oxygen (1O2) in dichloromethane. Evidence for the formation

Controlled Generation of Singlet Oxygen at Low Temperatures from Triphenyl Phosphite Ozonide

The usefulness of triphenyl phosphite ozonide for generating singlet oxygen is greatly increased by the use of pyridine in methanol as solvent, which permits the controlled thermal generation of singlet oxygen at temperatures as low as -100 deg C without

Regioselective oxygenations of s-trans dienes, silyl dienol ethers (SDEs), by triphenyl phosphite ozonide (TPPO) and its mechanistic study

The direct oxygenation of s-trans dienes, silyl dienol ethers (SDEs) 2, by triphenyl phosphite ozonide (TPPO) has been examined in detail. The regioselective oxygenation was found to give hydroperoxide 3, alcohol 4, ketone 5, dimer 6, and peroxy phosphate 7 with concomitant formation of triphenyl phosphate 8 and diphenyl trimethylsilyl phosphate 10. The formation of peroxy phosphate 7 was found for the first time in TPPO oxygenation reactions. The low temperature31P and1H NMR spectroscopic analyses proved the direct reaction of SDEs with TPPO without generation of singlet oxygen. The formation of the oxygenated products 3-7 is reasonably explained by the intervention of the zwitterion ZI, which can be formed by the nucleophilic attack of SDE to the central oxygen of the ozonide. The regioselective attack of SDE to the central oxygen of the ozonide was supported by the quantum chemical calculation (B3LYP/6-31G*).

A Reexamination of the Ozone-Triphenyl Phosphite System. The Origin of Triphenyl Phosphate at Low Temperatures

The reaction of ozone with triphenyl phosphite (P) at -78°C affords a labile 1:1 complex (PO3) together with small amounts of triphenyl phosphate (PO) (Q. E. Thompson, J. Am. Chem. Soc. 1961, 83, 845). In this work we found that the amount of PO present initially after complete ozonation of P in toluene was 12 ± 2% at -78°C and 11 ± 2% at -95°C. Partial ozonation of solutions of P in toluene at -78°C gave mixtures of P, PO, and PO3 whose composition changed with time as a result of the reaction of P with PO3 to give additional PO. Between -25 and -60 °C, the rate constant of the latter reaction is given by the expression log k (M-1 s-1) = (8.64 ± 0.04) - (11.44 ± 0.74) kcal/AT. This reaction at -78°C is too slow to account for the PO formed during the ozonation, which is proposed to arise instead by competitive reactions of an intermediate. The solubility of PO in toluene at -78°C was measured as 0.06 M, and that of PO3 about 6 times greater.

VOLTAMMETRIC STUDY OF REACTIONS OF TRIPHENYLPHOSPHITE OZONIDE

The electrochemical characteristics of reduction of triphenylphosphite ozonide at a stationary platinum electrode were determined in acetonitrile at between -30 and -11 deg C.The feasibility of employing voltammetric methods to investigate the reactions of phosphite ozonides was demonstrated in a model study of the kinetics of the thermal decomposition of (C6H5O)3PO3 and its reaction with triphenylphosphite. Keywords: kinetics, decomposition, ozonide, triphenylphosphite, ozonation, voltammetry.

CHEMILUMINESCENCE UPON DECOMPOSITION OF THE OZONIDE OF TRIPHENYLPHOSPHITE

We have studied the spectral composition of luminescence and the kinetics of attenuation of chemiluminescence upon thermal decomposition of the ozonide of triphenylphosphite.We have established that the emitter of chemiluminescence in the IR region is singlet oxygen, and the emitter of chemiluminescence in the visible region is triphenylphosphate.

OZONIDES DU PHOSPHORE STABILITE ET STEREOCHIMIE

A phosphorus ozonides series was obtained by reaction of ozone on various phosphites (1a-13a).The oxidative addition of ozone leads to trioxophosphetane ring formation branched on pentacoordinated (1b-9b) or hexacoordinated (10b-13b) phosphorus.The stability and stereochemistry of these compounds were studied.

Successive Displacements of Phenoxy by Methoxy Groups in Triphenyl Phosphite Ozonide: Mechanism of the Accelerated Singlet Oxygen Formation with Pyridine and Methanol

The ozonides from triphenyl phosphite, methyl diphenyl phosphite, and phenyl dimethyl phosphite form a series (1-3) which liberate singlet thermally at rates incresing by an order of magnitude for each substitution of methoxy for phenoxy.Trimethyl phosphite ozonide (4) fits in this series, although the very low temperature limit of its stability has not been determined.When triphenyl phosphite ozonide (1) is treated with methanol and pyridine in methylene chloride and yields singlet oxygen at an accelerated rate, the phenyl methyl phosphates 6 and 7 and trimethyl phosphate (8) are produced in a total amount corresponding to the singlet oxygen evolved.The lower the temperature, the greater the predominance of trimethyl phosphate (8) in the product.Each of the mixed phosphite ozonides 2 and 3 is in turn subject to accelerated singlet oxygen formation by the action of methanol and pyridine; in each case the phosphates formed contain at least one more methoxy group than the starting ozonide.These facts establish the mechanism of the accelerated singlet oxygen liberation as a successive displacement of phenoxy by methoxy groups on the initial phosphite ozonide, each newly formed aliphatic-aromatic phosphite ozonide decomposing thermally at its own increased rate.

PHOSPHORUS OZONIDES ADDUCTS

Ozone reacts quantitatively on tricoordinated and dicoordinated Phosphorus Compounds.The oxidative addition of ozone on phosphites leads to pentacoordinated or hexacoordinated phosphorus adducts.These adducts are unstable in solution.The decomposition gives the corresponding phosphoric ester with singlet oxygen evolution.In the same conditions, ozone reacts on diphosphene and gives after double bond rupture an adduct: the metaphosphonate.The relative stabilities and oxidative properties are discussed.

STABILISATION D'OZONIDES DU PHOSPHORE

We have obtained phosphorus ozonides (3b, 4b and 5b) in which phosphorus atom is hexacoordinated.In solution, these adducts are more stable than pentacovalent phosphorus homologs (ΔG*=23 kcal.mole-1 for 4b)