39190-67-5Relevant academic research and scientific papers
Enantiomerically pure quaternary ammonium salts with a chiral alkyl chain N(CH3)(n-C3H7)2(sec-C4H9)I: Synthesis and physical studies
Gheorghe, Ruxandra,Chamoreau, Lise-Marie,Kapitan, Josef,Ovanesyan, Nikola S.,Aldoshin, Sergei M.,Hecht, Lutz,Barron, Laurence D.,Train, Cyrille,Gruselle, Michel
, p. 1085 - 1091 (2008)
A pair of enantiomerically pure quaternary ammonium salts with a chiral side chain, methyl-(R)-(1-methylpropyl)di(n-propyl)ammonium iodide 1 and methyl-(S)-(1-methylpropyl)di(n-propyl)ammonium iodide 2, and the related racemate, methyl-(rac)-(1-methylpropyl)di(n-propyl)ammonium iodide 3, were synthesized through a reductive alkylation procedure, starting from enantiomerically pure and, also, racemic forms of (rac)-(1-methylpropyl)amine. A spectroscopic chiroptical signature in solution was provided by the Raman optical activity spectra of compounds 1 and 2. The crystallographic structures of 1, 2, and 3 were examined by single crystal X-ray diffraction. 1 crystallizes in the tetragonal space group P43212 (no. 96), a = b = 12.826 (2) ?, c = 17.730 (2) ?, V = 2916.9 (5) ?3, Z = 8, Flack coefficient 0.04 (2). 2 crystallizes in the tetragonal space group P41212 (no. 92), a = b = 12.842 (1) ?, c = 17.749 (2) ?, V = 2927.0 (5) ?3, Z = 8, Flack coefficient 0.05 (2). The crystal structures and space groups for 1 and 2 are enantiomorphs and the crystallographic investigation confirmed the absolute configuration of the stereocenter in both compounds. 3 crystallizes in the monoclinic space group P21/n(no. 14), a = 8.178 (1) ?, b = 14.309 (2) ?, c = 12.328 (2) ?, β = 96.811 (6)°, V = 1432.4 (2) ?3, Z = 4. Chirality 20:1085-1091, 2008.
ELECTROCHEMICAL REDUCTIVE AMINATION. I. AMINATION OF ALIPHATIC KETONES BY PRIMARY AMINES
Smirnov, Yu. D.,Tomilov, A. P.
, p. 42 - 48 (2007/10/02)
The reductive amination of aliphatic ketones in aqueous solutions of primary amines was realized by an electrochemical method.The best yields of the secondary amines were obtained at lead and cadmium cathodes in an aqueous electrolytic solution at pH 11-12.Elongation and branching in the carbon chain of the radicals both of the ketone and of the primary amine lead to a reduction in the yield of the secondary amine.The yield of the secondary amine is mainly determined by the rate of the chemical reaction leading to the formation of the azomethine compound, preceding the electrochemical reduction stage.
ELECTROCHEMICAL REDUCTIVE AMINATION. II. AMINATION OF ALIPHATIC ALDEHYDES WITH PRIMARY AMINES
Smirnov, Yu. D.,Pavlichenko, V. F.,Tomilov, A. P.
, p. 374 - 380 (2007/10/02)
The formation of a secondary amine by the electrolysis of an aqueous solution containing an aldehyde and a primary amine was studied.The formation of the secondary amines passes through the intermediate stage of an aldimine.The highest yield of secondary amine is attained at a molar ratio of primary amine to aldehyde of 1.2:1.As electrode material lead, cadmium, zinc, and copper may be used.As supporting electrolyte a phosphate buffer with a pH close to the pKa of the primary amine is recommended.By the method developed 32 amines with various structures were synthesized.
