One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, Quality Control of 1-Phenyl-1,2,3,4-tetrahydroisoquinoline, such as the rate of change in the concentration of reactants or products with time.In a article, mentioned the application of 22990-19-8, Name is 1-Phenyl-1,2,3,4-tetrahydroisoquinoline, molecular formula is C15H15N
Prototype Pictet-Spengler reactions catalyzed by superacids. Involvement of dicationic superelectrophiles
The Pictet-Spengler reaction, an acid-catalyzed intramolecular cyclization of intermediate imines of 2-arylethylamine to give 1,2,3,4- tetrahydroisoquinolines, has long been limited to active substrates which bear strongly electron-donating groups such as a methoxy or a hydroxy group on the cyclizing benzene ring. In this paper, we present superacid-catalyzed Pictet-Spengler reactions of imines of 2-phenethylamine, including the prototype Pictet-Spengler reaction of N-methylene-2-phenethylamine, to give the parent and 1-substituted 1,2,3,4-tetrahydroisoquinolines in moderate to high yields. The yields are dependent on the acidity of the media. A linear relationship was found between the rate of the cyclization and the acidity of the reaction media in kinetic studies of N-methylene-2-phenethylamine and related imines, strongly supporting the intervention of an additional protonative activation of the N-protonated imines, that is, the involvement of dicationic superelectrophiles, N,N-diprotonated imines (ammonium- carbenium dications). We further found that the prototype cyclization of the parent N-methylene-2-phenethylamine is also catalyzed by TFA to give 1,2,3,4- tetrahydroisoquinoline in good yield, although the cyclization is significantly slower than that catalyzed by superacids. The prototype Pictet- Spengler cyclization of N-methylene-2-phenethylamine can thus take place both through the monocation (the N-monoprotonated imine) and the dication (the N,N-diprotonated imine), the latter reaction being predominant in superacids.
Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. Quality Control of 1-Phenyl-1,2,3,4-tetrahydroisoquinoline, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 22990-19-8, in my other articles.
Reference£º
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem