56687-95-7

Upstream product

• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 62-53-3 aniline 
• 1197040-29-1 phenyl isocyanate 
• 68-12-2 N,N-dimethyl-formamide 
• 407-25-0 trifluoroacetic anhydride 
• 74431-53-1 N,N-dimethyl-N'-phenylformamidine 

Downstream Products

• 68-12-2 N,N-dimethyl-formamide 
• 122-79-2 Phenyl acetate 
• 1227476-15-4 Azobenzene 
• 88-75-5 2-hydroxynitrobenzene 
• 15568-92-0 5-(N-phenyl)-aminomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione 

Relevant academic research and scientific papers

Visible Light-Induced Aerobic Epoxidation of α,β-Unsaturated Ketones Mediated by Amidines

An aerobic photoepoxidation of α,β-unsaturated ketones driven by visible light in the presence of tetramethylguanidine (3b), tetraphenylporphine (H2TPP), and molecular oxygen under mild conditions was revealed. The corresponding α,β-epoxy ketones were obtained in yields of up to 94% in 96 h. The reaction time was shortened to 4.6 h by flow synthesis. The mechanism related to singlet oxygen was supported by experiments and density functional theory (DFT) calculations.

Formamidines - Versatile ligands for zinc-catalyzed hydrosilylation and iron-catalyzed epoxidation reactions

In the present study the abilities of catalysts modified by formamidine ligands have been examined in the zinc-catalyzed hydrosilylation of ketones and the iron-catalyzed epoxidation of stilbene, In case of hydrosilylation diethylzinc combined with easily accessible formamidine ligands allow for the efficient reduction of various aryl and alkyl ketones. By using a convenient in situ catalyst system high turnover frequencies up to more than 1.000 h -1 and a broad functional group tolerance were achieved. Moreover, the formamidine ligands were successfully applied, in the iron-catalyzed epoxidation of stilbene with hydrogen peroxide in good yield and chemoselectivity.

Unexpected formation of N,N-disubstituted formamidines from aromatic amines, formamides and trifluoroacetic anhydride

An intriguing selectivity towards the formation of the formamidine was observed upon the reaction of an amine with sodium hydride and trifluoroacetic anhydride in dimethyl formamide. Various aromatic amines were reacted with a series of N,N-disubstituted formamides as a solvent under the influence of trifluoroacetic anhydride to thoroughly probe this behaviour. A trend in selectivity is discussed and a proposed mechanism for the reaction is also presented.

Dication C(R1)-N(R2)2 synthons and their use in the synthesis of formamidines, amidines, and α-aminonitriles

A combination of amides and 2-pyridinesulfonyl chloride was evaluated as synthons of the dication C(R1)-N(R2)2/2+. When the substrates were primary amines, high yields of formamidines and amidines were obtained. When the substrates were α-aminoamides, α-aminonitriles were obtained. Through this process, naturally occurring α-aminoacids can be transformed into chiral α-aminonitriles with complete retention of stereochemical configuration. All reactions proceed rapidly at room temperature, and normally finish within 10 min, with yields ranging from 80 to 95% for most cases. Among the sulfonyl chlorides examined, 2-pyridinesulfonyl chloride stands out in both reaction rate and selectivity of formamidine or amidine versus sulfonyl amide. The scope and limitations of the reaction among different types of amides as synthons and amines as substrates were examined. (C) 2000 Elsevier Science Ltd.

PyBroP: A convenient activator for the synthesis of formamidines

PyBroP was used as a convenient coupling reagent in the synthesis of formamidines from aliphatic and aromatic primary amines and N,N- dimethylformamide.

An efficient and convenient synthesis of formamidines

A set of new reagents, aryl sulfonyl chlorides, were used as coupling agents in the syntheses of formamidines from primary amines and N,N-dimethyl formamide in excellent yields.

1-Methyl-2(alkylimino)pyrrolidines and 1-methyl 2(cycloalkylimino) pyrrolidines

Amidines are one of the strongest organic bases and find application where this property is needed, such as in phase transfer catalysis in the form of their substituted derivatives. Their use, however, has been hampered by their expensive nature due to on

STEREOSPECIFIC FORMATION OF AMIDINES BY 1,1-ADDITION OF AMINES TO ISOCYANIDES

Addition of secondary amines to isonitriles in the presence of AgCl at low temperature gives isolable but thermodynamically unstable Z-amidines; only the more stable 6E undergoes ring expansion to the imidazoline 7.

Isomerisation about the C-N and C=N Bonds of E- and Z-Amidines

The unstable Z-formamidines are 'frozen' in the perpendicular configuration (6); ready isomerisation occurs to the E-form (2).