74974-19-9Relevant articles and documents
Odorous products of the chlorination of phenylalanine in water: Formation, evolution, and quantification
Freuze, Ingrid,Brosillon, Stephan,Herman, Dorine,Laplanche, Alain,Democrate, Christian,Cavard, Jacques
, p. 4134 - 4139 (2004)
To explain some of the possible origins of an odor episode which took place in a drinking water supply in the region of Paris (France), the chlorination reaction in water of phenylalanine was studied. This amino acid was chosen for first experiments becau
Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron
Chen, Dongping,Li, Kaidi,Tang, Wenjun,Xu, Guangqing,Xu, Ronghua,Zhou, Mingkang
supporting information, p. 10337 - 10342 (2020/07/04)
We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method signifies the generality of diboron-enabled [3,3]-sigmatropic rearrangement.
Metal-free, one-pot oxidative conversion of aldehydes to primary thioamides in aqueous media
Yadav, Arvind K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
supporting information, p. 408 - 416 (2014/01/06)
One-pot tandem reactions of a variety of aldehydes with aqueous ammonia, molecular iodine, and O,O-diethyl dithiophosphoric acid readily afford the corresponding primary thioamides. This is an inexpensive, practical, and metal-free way of accessing various thioamides from aldehydes in aqueous media. The pure products are obtained simply by filtration followed by successive washing with aqueous sodium thiosulfate and water. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
Kinetics and mechanism of the oxidation of some α-amino acids by butyltriphenylphosphonium dichromate
Panday, Dinesh,Dilsha,Kothari, Seema
experimental part, p. 816 - 821 (2010/07/13)
The oxidation of a series of nine α-amino acids by butyltriphenylphosphonium dichromate (BTPPD) in glacial acetic acid in the presence of toluene β-sulphonic acid (TsOH), leads to the formation of corresponding aldimines. The reactions are of first order with respect to BTPPD whereas the second order dependence is observed with respect to each the amino acid and hydrogen ion. The oxidation of perdeuterioglycine showed the absence of a kinetic isotope effect (kH/kD = 1.01 at 308 K). The reactions showed an excellent correlation with Taft's σ* substituent constants, the reaction constant being negative. The oxidation of alanine was studied in nineteen different organic solvents. The solvent effect was analyzed using Kamlet's and Swain's multiparametric equations. The analyses of solvent effect indicated the importance of the cation-solvating power of the solvent. Suitable mechanisms for the oxidation process are postulated.
Determining the scope of the lanthanide mediated, sequential hydroamination/C-C cyclization reaction: Formation of tricyclic and tetracyclic aromatic nitrogen heterocycles
Molander, Gary A.,Pack, Shawn K.
, p. 10581 - 10591 (2007/10/03)
The scope of the lanthanide mediated, sequential hydroamination/C-C cyclization reaction was determined for the formation of tricyclic and tetracyclic aromatic nitrogen heterocycles. An array of ring sizes was explored to determine the diastereoselectivity. The electronic characteristics of the aromatic ring was also varied to determine how it affected the cascade reaction. It was found that the benzo[a]quinolizine and the pyrido[2,1,a]isoindolizine ring systems formed with the highest diastereoselectivity (>20:1), regardless of the electronic characteristics of the aromatic ring. Additionally, a tetracyclic indole nitrogen heterocycle was formed with a 2.3:1 diastereomeric ratio. A novel procedure for substrate preparation is also presented.
Cross Mannich Reaction of Aldehydes; Efficient Synthesis of Substituted Pyridines
Winter, Andreas,Risch, Nikolaus
, p. 2667 - 2670 (2007/10/03)
Symmetrically and unsymmetrically substituted pyridines were obtained in highly efficient one-pot procedures starting from α-unbranched aldehydes and iminium salts.
Ligation and Reduction of Iron(III) Porphyrins by Amines. A Model for Cytochrome P-450 Monoamine Oxidase
Castro, C. E.,Jamin, Mary,Yokoyama, W.,Wade, Ruth
, p. 4179 - 4187 (2007/10/02)
The scope and mechanism of the ligation and reduction of iron(III) porphyrins by amines are presented.The reaction is general and proceeds with the overall stoichiometry 2PFe(III)Cl + 5RNH2 -> 2PFe(II)(H2NR)2 + R'CH=NH + 2RNH3(1+)Cl(1-).Imines are the only amine-derived products.The ability of the amine to coordinate iron and its possession of a >CHNH moiety are essential for reduction.The reaction path antails two successive reversible ligation steps followed by two one-electron reductions of the bis(amine)-ligated low-spin iron(III) adduct.In benzene the kinetics are biphasic.The second ligation is rate limiting 1(ligation > k(reduction) > k2(ligation)>.In dimethylformamide the first reduction step is rate limiting.The influence of nonreducing amines, porphyrin substituent, axial ligands, and deuteration of the substrate upon the kinetics leads to the formulation of the first reduction as a reversible outer-sphere electron transfer to the porphyrin periphery.This is followed by a rapid conversion of the generated aminium cation radical to an α-aminocarbinyl radical.The latter completes the reduction in an irreversible second step.The relevance of this chemistry to related transformation catalyzed by cytochrome P-450 is discussed.
