79121-27-0

Upstream product

• 109423-11-2 C₂₄H₁₈N₆ 
• 50-00-0 formaldehyd 
• 873-74-5 4-Aminobenzonitrile 
• 79121-25-8 1,4-Bis(p-cyanophenyl)-1,4-dimethyl-2-tetrazene 

Downstream Products

• 97860-68-9 N-(4-cyanophenyl)-N-methylformamide 
• 4714-62-9 4-cyano-N-methylaniline 
• 1643531-65-0 (E)-tert-butyl 3-[N-(4-cyanophenyl)-N-(methyl)amino]acrylate 

Relevant academic research and scientific papers

Iron-Catalyzed Regioselective α-C-H Alkylation of N-Methylanilines: Cross-Dehydrogenative Coupling between Unactivated C(sp3)-H and C(sp3)-H Bonds via a Radical Process

The iron-catalyzed α-C-H alkylation of N-methylanilines without any directing group by cross-dehydrogenative coupling between unactivated C(sp3)-H and C(sp3)-H bonds has been established for the first time, which provides a good complement to C(sp3)-H activation reactions and expands the field of Fe-catalyzed C-H functionalizations. Many different C(sp3)-H bonds in cyclic alkanes, cyclic ethers, and toluene derivatives can be used as coupling partners. Mechanistic investigations including the radical reaction process, the main role of various reagents, and the kinetic isotope effect experiment were also described.

Expedient stereospecific Co-catalyzed tandem C-N and C-O bond formation of: N -methylanilines with styrene oxides

Cobalt(ii)-catalyzed stereospecific coupling of N-methylanilines with styrene oxides is developed via tandem C-N and C-O bond formation using tert-butyl hydroperoxide (TBHP) as an oxidant. Optically active epoxide can be reacted with high optical purity.

Stereospecific copper-catalyzed domino ring opening and sp3 C-H functionalization of activated aziridines with N-alkylanilines

Copper efficiently catalyzed nucleophilic ring opening, sp3 C-H functionalization, and C-N bond formation in the presence of tert-butyl hydroperoxide to afford functionalized imidazolidines starting from N-sulfonylaziridines and Nalkylanilines. The products were obtained in high optical purities (95 → 99% ee) with excellent functional group tolerance.

Direct condensation of functionalized sp3 carbons with formanilides for enamine synthesis using an in situ generated HMDS amide catalyst

The efficient synthesis of functionalized enamines including β-enaminoesters was effectively accomplished by the direct condensation of functionalized sp3 carbanions such as acetates with formamides using in situ generated HMDS base from catalytic cesium fluoride and stoichiometric tristrimethylsilylamine. This journal is the Partner Organisations 2014.

Revisitation of Formaldehyde Aniline Condensation. VII. 1,3,5-Triarylhexahydro-sym-triazines and 1,3,5,7-Tetraaryl-1,3,5,7-tetrazocines from Aromatic Amines and Paraformaldehyde

A product study of the reaction between a number of aromatic amines substituted with widely different groups and paraformaldehyde in inert solvents was performed and found to yield 1,3,5-triaryl-1,3,5-hexahydrotriazines, 1,3,5,7-tetraaryl-1,3,5,7-tetrazocines and formaminals.It was not possible to correlate the product outcomes with the actual structure of the amine substrate.The X-ray diffraction structural determination of 1,3,5-tri-(t-butylphenyl)- (1b) and 1,3,5-tri-(m-fluorophenyl)-1,3,5-hexahydrotriazine (1c) showed the diaxial arrangement of the N-substituents.

Photobenzidine Rearrangements. 7. Disproportionation and Recombination of N-Methylarylamino Radicals in the Photodecomposition of 1,4-Bis(p-cyanophenyl)-1,4-dimethyl-2-tetrazene and Other 2-Tetrazenes

The photochemical decomposition of 1,4-bis(p-cyanophenyl)-1,4-dimethyl-2-tetrazene (1c) in 1,2-dimethoxyethane (DME) was studied in detail.It was deduced that N-methyl-p-cyanoanilino radicals are formed and undergo three reactions: recombination into 1,2-bis(p-cyanophenyl)-1,2-dimethylhydrazine (2c, 21 percent), disproportionation (70 percent) into N-methyl-p-cyanoaniline (3c) and N-methylene-p-cyanoaniline (4c), and hydrogen atom abstraction (7 percent).A small amount of a p-semidine is thought to be formed also.These deductions were made from quantitative high-pressure LC measurements of yields of 2c, 3c, p-cyanoaniline (5c), and formaldehyde, the last two products arising from hydrolysis of 4c.Quantitative measurement of the conversion of 4c into 3c by hydrogenation and by trapping of radicals with butyl mercaptan was also used.Approximately 10 percent of 2e is formed in a solvent cage.Disproportionation also appears to occur within the cage.Less detailed studies were carried out with 1,4-diphenyl-1,4-dimethyl-2-tetrazene (1d) and 1,4-bis(p-bromophenyl)-1,4-dimethyl-2-tetrazene (1e).Decomposition of 1d led to 40 percent of N,N'-dimethyldiphenylhydrazine (2d, 10 percent in cage) and 40 percent of disproportionation products.The remaining 20 percent of the 1d is thought to form a p-semidine (N,N'-dimethyl-N-phenyl-1,4-benzenediamine) and the dibenzocarbazole related to it.Radicals from the decomposition of 1e led to 37 percent of 1,2-bis(p-bromophenyl)-1,2-dimethylhydrazine (2e, 10 percent in cage), 47 percent of disproportionation, and 16 percent of hydrogen abstraction.