53759-17-4

Upstream product

• 10604-60-1 (1-iodoethyl)benzene 
• 75-50-3 trimethylamine 
• 2449-49-2 dimethyl(1-phenylethyl)amine 
• 74-88-4 methyl iodide 
• 618-36-0 rac-methylbenzylamine 
• 19342-01-9 (S)-N,N-dimethyl-1-phenylethylamine 
• 613-91-2 acetophenone oxime 
• 2627-86-3 (S)-1-phenyl-ethylamine 

Downstream Products

• 100-42-5 styrene 
• 4013-34-7 3-phenyl-2-oxabutane 
• 20230-89-1 trimethylammonium iodide 
• 1857-74-5 2,3-diphenylbutane 
• 100-41-4 ethylbenzene 
• 98-85-1 1-Phenylethanol 
• 1343572-18-8 C₁₁H₁₈N⁽¹⁺⁾*C₁₀₆H₁₁₂N₈O₉*I^(1-) 
• 1343572-19-9 C₁₁H₁₈N⁽¹⁺⁾*C₁₀₆H₁₁₂N₈O₉*I^(1-) 
• 492-37-5 hydratropic acid 
• 131919-89-6 (R)-N,N,N-trimethyl-1-phenylethanammonium bromide 
• 585-71-7 (1-bromoethyl)benzne 
• 36043-87-5 N,N,N-trimethyl-1-phenylethan-1-aminium bromide 
• 52728-16-2 2-(dimethylaminomethylphenyl)ethylbenzene 

Relevant academic research and scientific papers

Chirality sensing of choline derivatives by a triple anion helicate cage through induced circular dichroism

Chirality sensing of choline derivatives is achieved by a self-assembled, racemic triple anion helicate cage which exhibits induced circular dichroism (ICD) upon encapsulation of a chiral guest. The host-guest interactions were illustrated by NMR, crystal

Induced circular dichroism of polyoxometalates via electrostatic encapsulation with chiral organic cations

To explore the principle of chiral induction in inorganic clusters, chiral organic cations with two stereocenters, R- and S-BPEA, are used to encapsulate a series of polyoxometalates (POMs) bearing different structures and transition absorption bands in a

Chiral conducting salts of nickel dithiolene complexes

Conducting and chiral [Ni(dmit)2] dithiolene salts were obtained by electrocrystallization of the radical [n-Bu4N][Ni(dmit) 2] salt in the presence of chiral, enantiopure trimethylammonium cations. Three different cations were investigated, namely, (R)-Ph(Me)HC- NMe3+, (S)-(tBu)(Me)HC-NMe3 +, and (S)-(1-Napht)MeHC-NMe3+, noted (R)-1, (S)-2, and (S)-3. Salts of 1:3 stoichiometry were obtained with (R)-1 and (S)-2, formulated as [(R)-1][Ni(dmit)2]3 and [(S)-2][Ni(dmit)2]3?(CH3CN)2. They both crystallize in the P212121 chiral space group, with three crystallographically independent complexes exhibiting different oxidation degrees. Another salt with 2:5 stoichiometry was isolated with (S)-3. The semiconducting character of the three salts (σ RT = 20-30 × 10-3 S cm-1) finds its origin in a strong electron localization, favored by the large number of crystallographically independent [Ni(dmit)2] complexes in these chiral structures and their association into weakly interacting dimeric or trimeric motifs. Racemic salts with the same cations, obtained only with difficulties with the tert-butyl-containing (rac)-2 cation, afforded similar trimerized structures. The observed unusual stoichiometry and strong charge localization is tentatively assigned to the size and anisotropic charge distribution of the cations.

Role of the hydrophobic effect in the transfer of chirality from molecules to complex systems: from chiral surfactants to porphyrin/surfactant aggregates

The interaction between the achiral sulfonated porphyrin 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin, H2TPPS 44-, and two chiral cationic surfactants has been studied by optical absorption, fluorescence, and circular dichroism (CD) spectroscopies. At surfactant concentrations above the critical micellar concentration (cmc) the porphyrin is included in the micellar aggregates, but it is CD silent. Below the cmc at a definite porphyrin/surfactant stoichiometry the formation of heteroaggregates with transfer of chirality to the porphyrin chromophore occurs. The preferred surfactant/porphyrin stoichiometry is 3:1, which suggests a structure driven by electrostatic and hydrophobic interactions between porphyrin and surfactant and dipolar and ionic interactions with the water solution. At surfactant concentrations above the cmc, depending on the protocol of preparation of the samples, the formation of the two kinds of aggregates can be observed, reversible for the simple surfactant micelles incorporating the porphyrin, but irreversible for the heteroaggregates.

Rhodium complexes with chiral counterions: Achiral catalysts in chiral matrices

The neutral complexes [Rh(I)(NBD)((1S)-10-camphorsulfonate)] (2) and [Rh(I)((R)-N-acetylphenylalanate)] (4) reacted with bis-(diphenylphosphino)ethane (dppe) to form the cationic Rh(I)(NBD)(dppe) complexes, 5 and 6, respectively, accompanied by their corresponding chiral counteranions. Analogously, 4 reacted with 4,4′-dimethylbipyridine to yield complex 7. Complexes 5 and 6 disproportionated in aprotic solvents to form the corresponding bis-diphosphine complexes 8 and 9, respectively. 8 was characterized by an X-ray crystal structure analysis. In order to form achiral Rh(I) complexes bearing chiral countercations new sulfonated monophosphines 13-16 with chiral ammonium cations were synthesized. Tris-triphenylphosphinosulfonic acid (H3TPPS, 11) was used to protonate chiral amines to yield chiral ammonium phosphines 14-16. Thallium-tris-triphenylphosphinosulfonate (Tl3TPPS, 12) underwent metathesis with a chiral quartenary ammonium iodide to yield the proton free chiral ammonium phosphine 13. Phosphines 15 and 16 reacted with [Rh(NBD)2]BF4 to afford the highly charged chiral zwitterionic complexes [Rh(NBD) (TPPS)2][(R)-N, N-dimethyl-1-(naphtyl)ethylammonium] 5 (17) and [Rh(NBD)(TPPS)2][BF4] [(R)-N, N-dimethyl-phenethylammonium]6 (18), respectively. Complexes 5, 6, and 18 were tested as precatalysts for the hydrogenation of de-hydro-N-acetylphenylalanine (19) and methyl-(Z)-(α) -acetoamidocinnamate (MAC, 20) under homogeneous and heterogeneous (silica-supported and self-supported) conditions. None of the reactions was enantioselective.

Syntheses of chiral homoazacalix[4]arenes incorporating amino acid residues: Molecular recognition for racemic quaternary ammonium ions

Chiral calixarene analogues incorporating amino acid residues into the macrocyclic rings were prepared from the cyclization reactions of bis(chloromethyl)phenol-formaldehyde tetramer with amino acid methyl ester in moderate yields. The macrocycles form a chiral concavity, which is induced by the chiral transmission from the point chirality of the amino acid residues to the phenol-formaldehyde tetramer unit. The macrocycles have the cavity π-basic enough to include the quaternary ammonium ion due to the cation-π interaction and can serve as a shift reagent for racemic ammonium ions during 1H NMR analysis.

Efficient NMR Enantiodifferentiation of Chiral Quats with BINPHAT Anion

(Matrix Presented) Hexacoordinated phosphorus BINPHAT anion is an efficient NMR chiral shift agent for quaternary ammonium cations (quats) leading to large separations (ΔΔδ up to 0.29 ppm) of the proton signals of the enantiomers.

Stereochemistry of Photosolvolysis of (-)-1-Phenylethyltrimethylammonium Iodide in Water and in Methanol, and Nucleophile Capture Ratios during Photosolvolysis of Some Benzylammonium Salts

The photosolvolysis of (-)-1-phenylethyltrimethylammonium iodide in water or methanol is characterised by extensive racemisation accompanied by some net configurational inversion, a result similar to that generally observed in thermal solvolysis via ion-pairs at chiral secondary centres.Recovered quaternary salt from the photolysis in water is only slightly if at all racemised, while likewise there is no observable epimerisation at nitrogen in recovered benzylammonium salts following photolysis in methanol of suitable derivatives of camphidine, trans-decahydroquinoline, and 4-phenylpiperidine.A strong preference for formation of the methyl ether rather than the alcohol is exhibited on either photochemical or thermal solvolysis of 1-p-methoxyphenylethyltrimethylammonium iodide in aqueous methanol, but nucleophile capture ratios during photosolvolysis of simple benzyltrimethylammonium salts in this mixed solvent system are much lower.