74157-87-2

Upstream product

• 621-06-7 2,N-diphenylacetamide 
• 103-82-2 phenylacetic acid 
• 103-80-0 phenylacetyl chloride 

Downstream Products

• 14181-75-0 N-(2-Phenylethenylidene)aniline 
• 1239867-65-2 3-methylbut-2-en-1-yl N,2-diphenylacetimidate 

Relevant academic research and scientific papers

The Diels-Alder cyclization of ketenimines

A Diels-Alder reaction between cyclopentadiene and a variety of ketenimines is reported. A copper(I)-bis(phosphine complex catalyzes the cycloaddition across the C - N bond of the ketenimine in a [4 + 2] reaction to give an enamine intermediate that is hy

Branch-selective synthesis of oxindole and indene scaffolds: Transition metal-controlled intramolecular aryl amidation leading to C3 reverse-prenylated oxindoles

In an effort to access biologically important scaffolds, a concise branch-selective synthesis of C3 tertiary oxindoles by Cu(I)-catalyzed aryl amidation and 2,2-dimethyl indene by Pd(0)-catalyzed Heck cyclization has been accomplished from acyclic reverse-prenylated intermediates. Oxindole C3-enolate generation using NaH followed by alkylation in the presence of appropriate electrophiles provides a novel route to quaternary C3 reverse-prenylated oxindoles.

Facile synthesis of bicyclic amidines and imidazolines from 1,2-diamines

A facile synthesis of chiral bicyclic amidines and imidazolines from readily available 1,2-diamines has been developed. The reported synthetic strategy relies on an intramolecular cyclization which involves a carboxylic amide derived imidoyl chloride as a

Rapid Acid-catalysed and Uncatalysed Hydration of Ketenimines

The rates of hydration of a series of ketenimines (9) have been examined in water (μ 1.0; 25 deg) over the pH range 2-13.Three mechanisms of hydration to the amides (8) were noted: (a) general acid catalysis by proton transfer from H3O(1+) in the pH range 2-7 (giving kH3O(1+)/kD3O(1+) 2.65); (b) general acid catalysis by H2O at pH > 7 (where kH2O/kD2O = 4.8); (c) rate determining HO(1-) attack.The last mechanism was only shown by N-arylketenimines, e.g. (9e); other N-alkylketenimines continue to react by rate-determining proton transfer from water even at pH 13.This result is confirmed by the incorporation of just one deuterium when (9a) reacted in acidic or basic D2O, while the deuteriated ketenimine (9f) does not loose the label on the reaction in water.Substituent effects are parallel for reactions involving H(1+) transfer from H3O(1+) or H2O; the major effects are obtained on changing substituents at carbon (the protonation site).For example, replacement of C-H by C-Me reduces the reactivity by 10-20-fold, while replacement of C-Me by C-Ph reduces the rate of hydration by >100-fold.Ammonium ions also generally react with ketenimines by rate-determining H(1+) transfer to the ketenimine followed by trapping of the nitrilium ion formed by the free amine.Only with the strongest amine base studied (piperidine) does direct nucleophilic attack on the ketenimine compete.