13652-09-0Relevant articles and documents
Thermocontrolled benzylimine-benzaldimine rearrangement over Nafion-H catalysts for efficient entry into α-trifluoromethylbenzylamines
Prakash, G.K. Surya,Glinton, Kevin E.,Panja, Chiradeep,Gurung, Laxman,Battamack, Patrice T.,T?r?k, Béla,Mathew, Thomas,Olah, George A.
experimental part, p. 607 - 611 (2012/02/13)
Nafion-H and Nafion SAC-13 are efficient solid Br?nsted acid catalysts for the preparation of trifluoromethyl ketimines from benzylamines and trifluoromethylated ketones in high yields. A finely tuned benzylimine- benzaldimine rearrangement by facile 1,3-hydrogen shift has been achieved for the formation of fluorinated benzaldimines in high yields by careful optimization of reaction conditions including attempts under microwave conditions and a flow system. These α-trifluoromethylated benzaldimines are efficient precursors for pharmaceutically important α- trifluoromethylated benzylamines, accessed through their direct acid hydrolysis.
Synthesis of alpha fluoroalkyl amines
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Page/Page column 3, (2008/06/13)
This invention describes the reaction of an alpha fluoroalkyl ketone with a bis(trialkylsilyl)amide to give a stable N-trialkylsilyl imine. Treatment of the N-trialkylsilyl imine with an alcohol leads to solvolysis of the trialkylsilyl group and yields a
Biomimetic reductive amination of fluoro aldehydes and ketones via [1,3]-proton shift reaction. Scope and limitations
Ono, Taizo,Kukhar, Valery P.,Soloshonok, Vadim A.
, p. 6563 - 6569 (2007/10/03)
A systematic study of azomethine-azomethine isomerizations of the N-benzylimines 2, derived from fluorinated aldehydes or ketones and benzylamine, has been made. The results reveal that, in sharp contrast to hydrocarbon analogs, fluorinated imines of 2 in triethylamine solution undergo isomerizations to give the corresponding N-benzylidene derivatives 5 (for 5/2 K > 32) in good isolated yields. The rates of the isomerizations depend on the starting imine structures and increase in the following order: aryl perfluoroalkyl ketimine 2m, per(poly)fluoroalkyl aldimine 2a,d-g, perfluoroaryl aldimine 2h, alkyl perfluoroalkyl ketimine 2i,j. The presence of chlorine or bromine atoms in the α-position to the C=N double bond of the starting imine favors a dehydrohalogenation reaction, giving rise to unsaturated products 6-9. The azomethine-azomethine isomerization was studied and proven to proceed essentially (>98%) intramolecularly with isotope exchange experiments. High chemical yields, the simplicity of the experimental procedure, and the low cost of all reagents employed make this biomimetic transamination of fluorocarbonyl compounds a practical method for preparing fluorine-containing amines of biological interest.