54522-91-7

Upstream product

• 3880-99-7 1-(13C)benzoic acid 
• 36712-21-7 methyl [carboxyl-¹³C]benzoate 
• 108-86-1 bromobenzene 

Downstream Products

• 10383-90-1 ⁽¹³⁾C-benzaldehyde 
• 57742-41-3 <α-¹³C>Benzylchlorid 
• 69838-86-4 [α-13C]benzyl bromide 
• 52947-05-4 [α-13C]benzoyl chloride 
• 3880-99-7 1-(13C)benzoic acid 
• 23351-79-3 phenyl-α-[¹³C]-acetylene 
• 61415-29-0 1,1-dibromo-2-[¹³C]-styrene 
• 116204-80-9 Cyclohexyl phenyl ketone 
• 181470-34-8 C₁₃⁽¹³⁾CH₁₆Cl₂ 
• 181470-36-0 C₁₃⁽¹³⁾CH₁₆Br₂ 
• 181470-30-4 phenyl-α-[¹³C]acetylenic triflone 
• 79341-52-9 1,2-Diphenyl-<1,2-13C2>ethan 
• 80607-11-0 1-Phenyl-<1,2-13C2>cyclohexan 
• 80607-18-7 1-Phenyl-<1,3-13C2>cyclohexan 

Relevant academic research and scientific papers

Well-defined silica-supported zirconium-benzyl cationic species: Improved heterogenization of single-site polymerization catalysts

Zr(CH2Ph)4 (1) was grafted onto a recently disclosed hybrid material based on amorphous silica that features unique phenol grafting sites {[(≡SiO)2(AlOC6H4OH)(Et 2O)] (H)}. A monopodal trib

Shapes of dendrimers from rotational-echo double-resonance NMR

The solid-state shape, size, and intermolecular packing of a fifth-generation dendritic macromolecule were determined by a combination of site-specific stable-isotope-labeling, rotational-echo double-resonance (REDOR) NMR and distance-constrained molecula

Catalytic Enantioselective [2,3]-Rearrangements of Allylic Ammonium Ylides: A Mechanistic and Computational Study

A mechanistic study of the isothiourea-catalyzed enantioselective [2,3]-rearrangement of allylic ammonium ylides is described. Reaction kinetic analyses using 19F NMR and density functional theory computations have elucidated a reaction profile

Metathesis Reaction of Diazo Compounds and para-Quinone Methides for C-C Double Bond Formation: Synthesis of Tetrasubstituted Alkenes and Quinolinones

The para-quinone methides (p-QMs) are activated by Lewis acid and then attacked by diazo compounds. The following rearrangement leads to nitrogen gas extrusion and C-C double bond formation to constitute a metathesis reaction process. Therefore, the diazo

Asymmetric 1,2-Perfluoroalkyl Migration: Easy Access to Enantioenriched α-Hydroxy-α-perfluoroalkyl Esters

This study has led to the development of a novel, highly efficient, 1,2-perfluoro-alkyl/-aryl migration process in reactions of hydrate of 1-perfluoro-alkyl/-aryl-1,2-diketones with alcohols, which are promoted by a Zn(II)/bisoxazoline and form α-perfluoro-alkyl/-aryl-substituted α-hydroxy esters. With (-)-8-phenylmenthol as the alcohol, the corresponding menthol esters are generated in high yields with excellent levels of diastereoselectivity. The mechanistic studies show that the benzilic ester-type rearrangement reaction takes place via an unusual 1,2-migration of electron-deficient trifluoromethyl group rather than the phenyl group. The overall process serves as a novel, efficient, and simple approach for the synthesis of highly enantioenriched, biologically relevant α-hydroxy-α-perfluoroalkyl carboxylic acid derivatives.

Experimental and theoretical mechanistic investigation of the iridium-catalyzed dehydrogenative decarbonylation of primary alcohols

The mechanism for the iridium-BINAP catalyzed dehydrogenative decarbonylation of primary alcohols with the liberation of molecular hydrogen and carbon monoxide was studied experimentally and computationally. The reaction takes place by tandem catalysis through two catalytic cycles involving dehydrogenation of the alcohol and decarbonylation of the resulting aldehyde. The square planar complex IrCl(CO)(rac-BINAP) was isolated from the reaction between [Ir(cod)Cl]2, rac-BINAP, and benzyl alcohol. The complex was catalytically active and applied in the study of the individual steps in the catalytic cycles. One carbon monoxide ligand was shown to remain coordinated to iridium throughout the reaction, and release of carbon monoxide was suggested to occur from a dicarbonyl complex. IrH2Cl(CO)(rac-BINAP) was also synthesized and detected in the dehydrogenation of benzyl alcohol. In the same experiment, IrHCl2(CO)(rac-BINAP) was detected from the release of HCl in the dehydrogenation and subsequent reaction with IrCl(CO)(rac-BINAP). This indicated a substitution of chloride with the alcohol to form a square planar iridium alkoxo complex that could undergo a β-hydride elimination. A KIE of 1.0 was determined for the decarbonylation and 1.42 for the overall reaction. Electron rich benzyl alcohols were converted faster than electron poor alcohols, but no electronic effect was found when comparing aldehydes of different electronic character. The lack of electronic and kinetic isotope effects implies a rate-determining phosphine dissociation for the decarbonylation of aldehydes.

Well-defined silica-supported zirconium-benzyl cationic species: Improved heterogenization of single-site polymerization catalysts

Zr(CH2Ph)4 (1) was grafted onto a recently disclosed hybrid material based on amorphous silica that features unique phenol grafting sites {[(≡SiO)2(AlOC6H4OH)(Et2O)] (H)}. A monopodal tribe

Insights into the asymmetric heterogeneous catalysis in porous organic polymers: Constructing A TADDOL-Embedded chiral catalyst for studying the structure-activity relationship[ ]

Construction of porous organic polymers (POPs) as asymmetric catalysts remains as an important but challenging task. Herein, we exploit the "bottom-up" strategy to facilely synthesize an α,α, α,α-tetraaryl-1,3-dioxolane-4,5-dimethanol (TADDOL)-based chiral porous polymer (TADDOL-CPP) for highly efficient asymmetric catalysis. Constructed through the covalent linkages among the three-dimensional rigid monomers, TADDOL-CPP possesses hierarchical porous structure, high Brunauer-Emmett-Teller (BET) surface area, together with abundant and uniformly-distributed chiral sites. In the presence of [Ti(OiPr)4], TADDOL-CPP acts as a highly efficient and recyclable catalyst in the asymmetric addition of diethylzinc (Et2Zn) to aromatic aldehydes. Based on the direct observation of the key intermediates, the reaction mechanism has been revealed by solid-state 13C magic-angle spinning (MAS) NMR spectroscopy. In combination with the catalytic testing results, characterization on the working catalyst provides further information for understanding the structure-activity relationship. We suggest that the catalytic activity of TADDOL-CPP is largely affected by the structural rigidity, cooperative catalysis, local chiral environment, and hierarchical porous framework. We expect that the information obtained herein will benefit to the designed synthesis of robust POP catalysts toward practical applications.

Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines

Isotopic labelling studies were performed to probe a proposed 1,2-aryl shift in the gold-catalysed cycloisomerisation of alkynyl aziridines into 2,4-disubstituted pyrroles. Two isotopomers of the expected skeletal rearrangement product were identified usi

A m-benzyne to o-benzyne conversion through a 1,2-shift of a phenyl group

Pyrolysis of two differently labeled versions of 3-phenylphthalic anhydride shows that a m-benzyne can form the related o-benzyne through shift of a phenyl group. The highest energy point in the process is the transition structure for a reverse carbon-hyd