374623-32-2

Upstream product

• 1807-55-2 4,4'-methylenebis(N-methylaniline) 
• 100-61-8 N-methylaniline 

Downstream Products

• 1627849-45-9 bis(4-(methyl(2,2,2-trifluoroethyl)amino)phenyl)methanone 

Relevant academic research and scientific papers

Synthesis, Structure, and Properties of Amino-Substituted Benzhydrylium Ions – A Link between Ordinary Carbocations and Neutral Electrophiles

Optimized synthetic procedures for the straightforward access to eleven amino-substituted diarylmethylium tetrafluoroborates are described. These benzhydrylium ions cover a range of seven orders of magnitude in electrophilicity and provide a link between ordinary carbocations and neutral electrophiles. Five of these highly stabilized benzhydrylium tetrafluoroborates were characterized by single-crystal X-ray crystallography. While the experimentally determined bond lengths and angles in the solid state perfectly agree with those calculated by DFT methods for the gas phase and aqueous solution, crystal packing accounts for large differences in the twist angles of the aryl groups found in the solid state as compared to calculated structures.

Scope and Mechanisms of Frustrated Lewis Pair Catalyzed Hydrogenation Reactions of Electron-Deficient C￡C Double Bonds

Several phosphonium and ammonium triarylborohydrides, which are intermediates in hydrogenation reactions catalyzed by frustrated Lewis pairs, were synthesized in high yield under mild conditions from triaryl boranes, ammonium or phosphonium halides, and triethylsilane. The kinetics and mechanisms of the reactions of these hydridoborate salts with benzhydrylium ions, iminium ions, quinone methides, and Michael acceptors were investigated, and their nucleophilicity was determined and compared with that of other hydride donors.

Towards a comprehensive hydride donor ability scale

Rates of hydride transfer from several hydride donors to benzhydrylium ions have been measured at 20 °C and used for the determination of empirical nucleophilicity parameters N and sN according to the linear free energy relationship log k20 °C=sN(N+E). Comparison of the rate constants of hydride abstraction by tritylium ions with those calculated from the reactivity parameters sN, N, and E showed fair agreement. Therefore, it was possible to convert the large number of literature data on hydride abstraction by tritylium ions into N and sN parameters for the corresponding hydride donors, and construct a reactivity scale for hydride donors covering more than 20 orders of magnitude.

Hydride-donor abilities of 1,4-dihydropyridines: A comparison with π nucleophiles and borohydride anions

(Chemical Equation Presented) How are dihydropyridines like indoles? Both groups of compounds have similar nucleophilicity parameters N and are therefore suitable substrates for iminium-catalyzed reactions of α,β- unsaturated aldehydes. The N parameters of 1,4-dihydropyridines were derived from the rates of hydride transfer reactions to benzhydrylium ions (see scheme).