596-30-5

Usage

Uses

Used in Organic Synthesis:
Peroxide, bis(triphenylmethyl) (9CI) is used as an oxidizing reagent for the synthesis of various organic compounds. Its ability to facilitate oxidation reactions makes it a valuable component in the preparation of a range of organic molecules.
Used as a Polymerization Initiator:
In the polymer industry, Peroxide, bis(triphenylmethyl) (9CI) serves as a polymerization initiator. It helps to kick-start the process of polymer formation, making it an essential ingredient in the production of certain polymers.
Used in Radical Reactions:
Peroxide, bis(triphenylmethyl) (9CI) can participate in radical reactions, which are significant in various chemical processes. Its involvement in these reactions contributes to the synthesis of specific types of compounds that require radical intermediates.
It is important to handle Peroxide, bis(triphenylmethyl) (9CI) with care, as peroxides are generally unstable and can pose hazards if mishandled or combined with incompatible substances.

Upstream product

• 56-23-5 tetrachloromethane 
• 54040-66-3 benzoyl-trityl-diazene 
• 917-64-6 methyl magnesium iodide 
• 76-84-6 triphenylmethyl alcohol 
• 60-29-7 diethyl ether 
• 486-25-9 9-fluorenone 
• 30615-54-4 triphenylmethyl bromide 
• 6652-29-5 2-phenoxy-1,2-diphenylethanone 
• 4303-71-3 triphenylmethyl sodium 
• 596-43-0 bromo-triphenyl-methane 
• 4198-93-0 trityl hydroperoxide 
• 519-73-3 triphenylmethane 
• 2216-49-1 triphenylmethyl radical 
• 19112-42-6 pentaphenylethane 

Downstream Products

• 42732-53-6 1,2-diphenoxy-1,1,2,2-tetraphenylethane 
• 76-84-6 triphenylmethyl alcohol 
• 596-43-0 bromo-triphenyl-methane 
• 22870-21-9 bis-(4,4',4''-trinitro-trityl)-peroxide 
• 76-83-5 trityl chloride 
• 632-51-9 1,1,2,2-tetraphenylethylene 
• 108-95-2 phenol 
• 119-61-9 benzophenone 
• 59550-02-6 benzophenone diphenyl ketal 
• 5447-80-3 trityl phenoxide 
• 831-18-5 ditropenyl 
• 115226-95-4 8-Cyclohepta-1,3,6-trienyl-7,9-diphenyl-8H-cyclopenta[a]acenaphthylene 
• 115205-69-1 7,9,7',9'-Tetraphenyl-8H,8'H-[8,8']bi[cyclopenta[a]acenaphthylenyl] 
• 519-73-3 triphenylmethane 

Relevant academic research and scientific papers

Reduction of Dioxygen by Radical/B(p-C6F4X)3 Pairs to Give Isolable Bis(borane)superoxide Compounds

Triplet dioxygen was reduced by TEMPO or trityl radicals in the presence of two molar equivalents of the strong B(p-C6F4X)3 (X: F or H) boron Lewis acids under mild conditions to give the bis(borane)superoxide systems 2. T

The rearrangement of the trityloxy radical: Sherlock holmes' most recent case

Reopening the case: One hundred years after Wieland's original publication, the rearrangement of the trityloxy radical was studied by K. Ingold et al., who investigated the title reaction with the logical reasoning and intellectual prowess of true detecti

Reactions of titanium alcoholates Ti(OR)4 (R = n-Bu, t-Bu) with tertiary organic and organometallic hydroperoxides

tert-Butyl and cumyl hydroperoxides in the reactions with Ti(OR) 4 are reduced to alcohols with the evolution of oxygen via formation of titanium-containing peroxides and trioxides. The pathways of the reactions of Ti(OR)4 with triphenylelement hydroperoxides R3EOOH (E = C, Si, Ge) depend on element E and on the structure of R; the reactions involve the rearrangement of the peroxides, and with (n-BuO)4Ti the alkoxy group is oxidized either with preservation or with breakdown of the hydrocarbon skeleton. Pleiades Publishing, Inc., 2006.

Thermolysis of N-tetramethylpiperidinyl triphenylacetate: Homolytic fragmentation of a TEMPO ester

Thermolysis of N-tetramethylpiperidinyl triphenylacetate (7, Ph 3CCO2T, T = 2,2,6,6-tetramethylpiperidinyl) in benzene at 146 °C leads to the formation of triphenylmethane (Ph3CH, 80%), tetramethylpiperidine (TH, 91%), and tetraphenylmethane (Ph4C, 9%). First-order rate constants for the decomposition at 132.8 and 150.0 °C were 2.20 × 10-6 and 2.88 × 10-5 s-1, respectively. In benzene-d6 solvent the triphenylmethane was formed as Ph3CD to the extent of 20%, as determined by 1H NMR and mass spectrometry. The results are interpreted as showing that Ph 3CCC2T undergoes thermolysis by concerted two-bond scission with formation of Ph3C., tetramethylpiperidinyl radicals and CO2. The formation of Ph4C occurs by addition of Ph3C. to benzene, followed by hydrogen atom abstraction from the resulting adduct. Calculations using DFT methods at the B3LYP/6-311++G** level were used to elucidate the bond fission of HCO2T (2), and indicate that cleavage to HCO2. and T. is favored by 7.8 kcal mol-1 relative to cleavage to HC(·)=O and TO., in agreement with the experimental results. Copyright

Chemiluminescence during thermolysis of the (Ph3COOCPh3)n-Ph3C. peroxide containing captured triphenylmethyl radical

Chemiluminescence (CL) in the thermolysis of (Ph3COOCPh3)n-Ph3C. containing the triphenylmethyl radical captured during the synthesis of Gomberg's peroxide was found. Two CL emitters were identified: the triplet state of benzophenone (3Ph2CO*) and Ph3C.*. Ph3C.* is formed due to the energy transfer from the excited 3Ph2CO* generated in the disproportion of thermolysis intermediates, Ph3CO. radicals. This Ph3C.* luminescence is the first example of CL activation by an organic radical. Chemiluminescence during the thermolysis of Ph3COOCPh3 containing no Ph3C. is resulted from the emission of one emitter, 3Ph2CO*. The solid-phase CL was found during the oxidation of Ph3C. with dioxygen after the destruction of the crystalline lattice as a result of the thermolysis of the (Ph3COOCPh3)n-Ph3C. peroxide.

Novel Transformations of 1,2-Dioxetanes: β-Hydroxy Ethers by Addition of Alkyllithium Reagents

The reaction of 1,2-dioxetanes with alkyllithium reagents was investigated.The 3,3-disubstituted dioxetanes 2a,d and their halogen-substituted analogues 2b,c, which were used as probes to differentiate between the mechanistic alternatives (SN2 reactivity vs. single-electron transfer), reacted with n-BuLi to afford the β-hydroxy ethers 3a-d.Additionally, the epoxide 4 was obtained from dioxetanes 2b,c.The epoxide 5 and a small amount of acetophenone were found in the reaction of dioxetane 2c with triphenylmethyllithium, but only the minor part of the dioxetane-derived products could be identified.The observation of the epoxides 4 and 5 led to the mechanistic conclusion that nucleophilic attack (SN2 reactivity) is the most prominent process in this reaction.Key Words: Dioxetanes / Single electron transfer vs. nucleophilic attack / Ethers, β-hydroxy / Alkyllithium reagents

Arene Hydrides, 8. - SET vs. Nucleophilic Attack in Reactions of α-Bromoisobutyrophenone with Carbanions. Fragmentation of the Anion of Tetrahydrobianthracene

SET is the main reaction pathway between α-bromoisobutyrophenone (1) and the carbanions 7a-j- of diarylmethanes or disubstituted acetonitriles: 7- 7. + e and e + 1 Br- PhCOCMe2. (3).Main secon

The Reaction of Triphenylmethyl Bromide with Potassium O-Ethyl Dithiocarbonate (Potassium Xanthate) in Benzene and Cumene. A Note of Caution on the Application of the Radical Trap Dicyclohexylphosphine as a Probe for Electron-transfer-initiated Reactions of Triphenylmethyl Halides

The title reaction was studied under conditions where homolysis of the triphenylmethyl-to-sulphur bond of the dithiocarbonate 1d, its main product does not take place, or is negligible.Triphenylmethane 1c, triphenylmethanol 1g and benzophenone were obtained as further products under argon in cumene and in the presence of oxygen in benzene, respectively.This, together with ESR studies, indicates that part of the dithiocarbonate 1d results from single-electron transfer from O-ethyl dithiocarbonate anion to triphenylmethyl bromide 1a and out-of-cage recombination of triphenylmethyl and xanthyl radicals 6a.The main pathways leading to dithiocarbonate 1d appear, under the conditions studied, to be either a polar pathway consisting of two successive SN2'-type steps and/or an SET-type reaction with rapid in-cage recombination of triphenylmethyl and xanthyl radicals 6a.The hydrogen-atom donor dicyclohexylphosphine (DCPH) may not be used for trapping of the triphenyl radicals formed in the title reaction because DCPH acts as a single-electron donor towards bromide 1a, i.e. it itself generates triphenylmethyl radicals from the bromide.

Photoinduced Electron Transfer Oxygenation of Triphenylcarbenium Ion

Photooxidation of triphenylcarbenium ion in the presence of an electron donor affords bis(triphenylmethyl) peroxide via one electron transfer from the electron donor to the excited singlet state of triphenylcarbenium ion.

The Reaction of Triphenylmethyl Halides with Tributylphosphine and Tributylamine in Apolar Solvents

Triphenylmethyl bromide (1a) and chloride (1b) react with tributylphosphine and tributylamine in aromatic hydrocarbons by single electron transfer.The triphenylmethyl radicals produced (which may be detected by e.s.r. spectroscopy) abstract hydrogen from the solvent or the radical cations of the reagents to give triphenylmethane (1c), and are trapped by oxygen to give triphenylmethylperoxy radicals and subsequently benzophenone, triphenylmethanol (1d), and phenol.Tributylphosphine and tributylamine may act as hydrogen donors in the hydrogen-transfer processes involved in the formation of these oxygenation products.The halides (1a, b) and tributylphosphine furnish, in the absence of oxygen, in addition to triphenylmethane (1c) the tele substitution products (2a) and (2b), respectively.There is some evidence that the phosphonium salt (2a) is formed by an S'ET process, i.e. out-of-cage recombination of triphenylmethyl radicals and tributylphosphine radical cations or tributylphosphine.