50447-68-2

Upstream product

• 769-25-5 2,4,6-trimethylstyrene 
• 80707-10-4 2-chloro-1-(2,4,6-trimethylphenyl)ethanol 
• 50690-12-5 2-chloro-1-(2,4,6-trimethyl-phenyl)-ethanone 
• 487-68-3 mesytaldehyde 
• 593-71-5 Chloroiodomethane 
• 139016-19-6 (R)-1-(2,4,6-trimethylphenyl)-1,2-ethanediol 

Downstream Products

• 29924-37-6 β-(2,4,6-trimethylphenyl)-γ-butyrolactone 
• 5350-76-5 1-phenyl-2-(2,4,6-trimethylphenyl)ethanone 
• 173171-08-9 (R)-1-(2,4,6-trimethylphenyl)-2-(1-piperidinyl)ethanol 
• 1026982-52-4 Methanesulfonic acid (R)-2-piperidin-1-yl-1-(2,4,6-trimethyl-phenyl)-ethyl ester 

Relevant academic research and scientific papers

Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates

The generation of highly unstable chloromethylmagnesium chloride in a continuous flow reactor and its reaction with aldehydes and ketones is reported. With this strategy, chlorohydrins and epoxides were synthesized within a total residence time of only 2.6 s. The outcome of the reaction can be tuned by simply using either a basic or an acidic quench. Very good to excellent isolated yields, up to 97%, have been obtained for most cases (30 examples).

Remarkable increase in the rate of the catalytic epoxidation of electron deficient styrenes through the addition of Sc(OTf)3 to the MnTMTACN catalyst

The effect of Lewis acids on the catalytic activity of [Mn2(μ-O)3(TMTACN)2](PF6)2 in the epoxidation of styrenes using hydrogen peroxide as the oxidant has shown that the addition of Sc(OTf)3 at low catalytic loading results in a very significant increase in the efficiency of the catalyst and a reduction of the reaction time to only 3 minutes in most cases.

Catalytic Enantioselective Conversion of Epoxides to Thiiranes

A highly efficient and enantioselective Br?nsted acid catalyzed conversion of epoxides to thiiranes has been developed. The reaction proceeds in a kinetic resolution, furnishing both epoxide and thiirane in high yields and enantiomeric purity. Heterodimer formation between the catalyst and sulfur donor affords an effective way to prevent catalyst decomposition and enables catalyst loadings as low as 0.01 mol %.

Catalytic oxidation of alkenes with a surface-bound metalloporphyrin- peptide conjugate

A novel surface-bound metalloporphyrin-peptide conjugate was prepared and used to catalytically oxidize alkenes in the presence of iodosylbenzene. The catalyst was found to oxidize a number of alkene substrates in good yield under a variety of reaction conditions. Comparison to control experiments using surface-bound Mn(III)tetraphenylporphyrin showed differences in oxidation yields and ratios of oxidized products. Substrate competition experiments demonstrated the ability of the conjugate catalyst to discriminate between substrates on the basis of size. Both results suggest oxidative catalysis occurred between the porphyrin ring and the peptide chain with the peptide influencing the outcome of the reaction in accord with the catalyst design.

Epoxidation of styrenes by hydrogen peroxide as catalyzed by methylrhenium trioxide

Methylrhenium trioxide, CH3ReO3, catalyzes the oxidation of styrenes by hydrogen peroxide. Kinetic studies by three methods were carried out in acidic CH3CN/H2O (1:1 v/v) solutions. The catalytically-active species are the mono-peroxide, CH3Re(O)2(C2), A, and the bis-peroxide, CH3Re(O)(O2)2, B, which epoxidize a given styrene at a similar rate. The rate constants are relatively insensitive to steric hindrance, but increase with the nucleophilicity of the styrene, electron-donating groups on the olefinic carbons or on the aromatic ring enhancing the rate. The rate constants for meta- and para-substituted styrenes follow a linear Hammett relationship; correlation with σ+ gave ρ + -0.93 ± 0.05. In CD3CN, epoxides were observed by 1H NMR spectroscopy. ais-β-Methylstyrene and transβ-methylstyrene led to the cis epoxide and the trans epoxide, respectively. In acidic CH3CN/H2O, the major products were 1,2-diols. In some cases C-C bond cleavage products were also observed, the extreme case being β-methoxystyrene where the C-C bond was completely cleaved to yield benzaldehyde, formaldehyde, and methanol.

Electric Birefringences and Molecular Conformations of 2-Aryloxirans in Solution

Electric birefringence and dipole moment measurements have been made for five aryloxirans as solutes at 298 K.The data are analysed to obtain informations on the preferred solution-state conformations taking into account electronic and steric interactions