36981-54-1

Upstream product

• 141-53-7 sodium formate 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 2952-05-8 1,2-diphenylaziridine 
• 93-98-1 N-phenyl benzoyl amide 
• 124-38-9 carbon dioxide 
• 98-88-4 benzoyl chloride 

Downstream Products

• 93-98-1 N-phenyl benzoyl amide 
• 1197040-29-1 phenyl isocyanate 

Relevant academic research and scientific papers

Selective: N-formylation/N-methylation of amines and N-formylation of amides and carbamates with carbon dioxide and hydrosilanes: Promotion of the basic counter anions of the zinc catalyst

A catalyst composed of commercially available Zn(OAc)2 and 1,10-phenanthroline (phen) was effective in the N-formylation/N-methylation of amines using CO2 as the C1 source in the presence of hydrosilanes. An equimolar reaction of N-methylaniline with PhSiH3 under a CO2 atmosphere yielded the N-formylation product in 92% yield at 25 °C. Scale-up of the reaction using 10 mmol substrate was also successful in affording the desired product in 83% yield (1.1 g). This catalyst exhibits a high thermal stability and a turnover number (TON) of 385000 at 150 °C. In addition, the reaction of N-methylaniline in the presence of excess Ph2SiH2 produced N,N-dimethylaniline. Furthermore, our catalytic protocol was developed for the N-formylation of amides and carbamates, which have smaller pKa values and lower reactivities than the corresponding amines. The present Zn(OAc)2/phen catalyst was found to show versatility in the conversion of CO2 and amines into several functionalized organic chemicals under mild conditions. We propose that the basic counter anion (i.e., the acetate) of the catalyst activates both the Si-H and N-H bonds.

Laser flash photolysis of aziridines. Spectroscopic and kinetic characterization of azomethine ylides. Their [3 + 2] cyclization with alkenes and protonation by water-alcohols to yield iminium ions

The reactive intermediates generated by laser flash photolysis (λexc = 248 or 193 nm) of the aziridines (E)-1-butyl-2,3-diphenylaziridine 1, (E)-2,3-diphenylaziridine 2, 1,2-diphenylaziridine 3, 1-(p-methoxyphenyl)-2-phenylaziridine 4 and 1-butyl-2-phenylaziridine 5 in acetonitrile and alcohols as solvents were identified as the corresponding azomethine ylides and spectroscopically and kinetically characterized. The rate constants for the [3 + 2] reaction of the ylides with electron-deficient alkenes to give pyrrolidines are between 106 and 109 M-1 s-1. In the case of 1 and 2 iminium ions are produced by protonation (by H2O or ROH) of the ylides (also studied by time-resolved conductance). For this reaction, with MeOH as the proton donor, the kinetic isotope effect is k(MeO-H)/ k(MeO-D) = 5-7, from which it is concluded that the transition state for protonation of the carbanionic site of the ylide is linear.