21129-05-5

Upstream product

• 4217-66-7 1,2-dihydroxy-2-phenylpropane 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 98-83-9 isopropenylbenzene 
• 98-82-8 Isopropylbenzene 
• 1889-67-4 dicumene 
• 98-86-2 acetophenone 
• 72331-76-1 (+/-)-1-acetoxy-2-phenyl-2-propanol 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 79-21-0 peracetic acid 

Relevant academic research and scientific papers

Vicinal Difunctionalization of Alkenes under Iodine(III) Catalysis involving Lewis Base Adducts

The influence of a 2-pyridinyl substituent on the catalytic performance of aryl iodides as catalyst in iodine(III) chemistry was explored. An efficient Lewis base adduct between the pyridine nitrogen and the electrophilic iodine(III) center was identified and confirmed by X-ray analysis. This arrangement was shown to generate a kinetically competent superior catalyst structure for the catalytic dioxygenation of alkenes. It introduces the concept of Lewis base adduct formation as a kinetic factor in iodine(I/III) catalysis. (Figure presented.).

Iron-Catalyzed Dioxygenation of Alkenes and Terminal Alkynes by using (Diacetoxyiodo)benzene as Oxidant

An iron-catalyzed syn-diacetoxylation of alkenes and 1,2-oxyacetoxylation of terminal alkynes has been developed using (diacetoxyiodo)benzene as oxidant. A broad range of internal and terminal alkenes, including electron-rich as well as electron-deficient alkenes, gave the desired products in good to excellent yields with high diastereoselectivity (up to >99:1 dr). In addition the high catalytic activity of iron catalysis for the 1,2-oxyacetoxylation of terminal alkynes is also reported. The roles of catalyst, oxidant and other reaction parameters were evaluated for activation of the unsaturated bond.

Green diacetoxylation of alkenes in a microchemical system

The palladium-catalyzed diacetoxylation and trifluoromethanesulfonic acid-catalyzed diacetoxylation using inexpensive and environmentally friendly hydrogen peroxide and peracetic acid were successfully conducted with the help of microchemical technology.

The nature of the catalytically active species in olefin dioxygenation with PhI(OAc)2: Metal or proton?

Evidence for the protiocatalytic nature of the diacetoxylation of alkenes using PhI(OAc)2 as oxidant is presented. Systematic studies into the catalytic activity in the presence of proton-trapping and metal-complexing agents indicate that protons act as catalysts in the reaction. Using triflic acid as catalyst, the selectivity and reaction rate of the conversion is similar or superior to most efficient metal-based catalysts. Metal cations, such as Pd(II) and Cu(II), may interact with the oxidant in the initiation phase of the catalytic transformation; however, 1 equiv of strong acid is produced in the first cycle which then functions as the active catalyst. Based on a kinetic study as well as in situ mass spectrometry, a mechanistic cycle for the proton-catalyzed reaction, which is consistent with all experimental data presented in this work, is proposed.

Bis(NHC)-palladium(II) complex-catalyzed dioxygenation of alkenes

Bis(NHC)-Pd(II) complexes derived from l,l'-binaphthyl-2,2'-diamine (BINAM) were successfully first used to catalyze the dioxygenation of alkenes under mild conditions tolerant of air and moisture. Cationic NHC-Pd2+ diaquo complex 1e showed the highest catalytic activity to give 1,2dioxygenation products with good syn-diastereoselectivity for 1,2-disubstituted alkenes.

Efficient diacetoxylation of alkenes via Pd(II)/Pd(IV) process with peracetic acid and acetic anhydride

A palladium-catalyzed diacetoxylation of alkenes in the presence of peracetic acid and acetic anhydride was developed to produce diacetates efficiently and diastereoselectively. Due to its mild conditions, this method was suitable for a broad range of substrates encompassing conjugated and nonconjugated olefins.

SILAFUNCTIONAL COMPOUNDS IN ORGANIC SYNTHESIS. 27. (ISOPROPOXYDIMETHYLSILYL)METHYL GRIGNARD REAGENT: A NEW NUCLEOPHILIC HYDROXYMETHYLATING AGENT FOR ALDEHYDES AND KETONES

Nucleophilic hydroxymethylation of aldehydes and ketones has been achieved by the reaction with the (isopropoxydimethylsilyl)methyl Grignard reagent and the subsequent oxidative cleavage of the carbon-silicon bond.

The Reactions of Cerium(IV) Ammonium Nitrate and Cobalt(III) Acetate with 1,2-Diphenylethanes in Acetic Acid. Evidence against the Involvement of Radical Cations in the Side-chain Oxidation of Alkylbenzenes by Co(OAc)3

The oxidation of 1,2-diphenylethane and 2,3-dimethyl-2,3-diphenylbutane by cerium(IV) ammonium nitrate and Co(OAc)3 in acetic acid shows that a radical cation mechanism is plausible only in the reaction of the former oxidant.

Electron-transfer Processes: Oxidation of α- and β-Alkenylbenzenes by Peroxydisulphate in Acetic Acid

Oxidation of α- and β-unsaturated alkylbenzenes by peroxydisulphate in acetic acid gives side-chain acetoxylation with formation of the corresponding glycol diacetates and compounds (10), respectively.The reaction is catalysed by transition-metal salts, among which cupric acetate gives the best results.Generally, electron-releasing substituents on the benzene ring increase the yield and improve the selectivity.The same substrates are oxidized in water under Ag+ catalysis to the corresponding aldehydes.The different behaviour in the two solvents is ascribed to the difference in reactivity between the primary oxidation products and the starting olefin, whereas the initial oxidation step is suggested to occur in both cases via an electron-transfer process from the olefin to the sulphate radical anion.