87281-94-5

Upstream product

• 23099-05-0 3-methyl-N-phenylbenzamide 

Downstream Products

• 626-60-8 3-Chloropyridine 
• 23099-05-0 3-methyl-N-phenylbenzamide 
• 16527-88-1 Pyridine 1-oxide hydrochloride 
• 87281-83-2 3-Methyl-N-phenyl-N-pyridin-2-yl-benzamide 
• 425365-96-4 3-methyl-N-phenyl-benzimidic acid 4-cyano-phenyl ester 
• 425366-13-8 phenyl-m-tolylmethylidyne-ammonium 

Relevant academic research and scientific papers

Rhenium-catalyzed synthesis of 3-imino-1-isoindolinones by C-H bond activation: Application to the synthesis of polyimide derivatives

Polyimide solution: Synthesis of the title compounds from aromatic imidates and isocyanates in good to excellent yields by a rhenium-catalyzed C-H bond transformation is described. The reaction also proceeded in high yield on gram scale and could be applied to the synthesis of polyimide derivatives (see figure), which are highly soluble in organic solvents. Copyright

N-arylbenzonitrilium ions. Photochemical generation and effect of substituents in the phenyl rings on lifetimes in water and reactivity with azide ion

Nitrilium ions Ar-C≡N+-Ar′ have been studied by laser flash photolysis in aqueous solutions containing 20% acetonitrile. The cations were generated by photoheterolysis of benzimidate esters Ar-CZ=N-Ar′ (Z = -OC6H4-4-CN) with 4-cyanophenoxide as the photochemical leaving group. Rate constants for the reaction with water (kw), azide ion (kaz) and hydroxide (kOH) were measured. The cation Ph-C≡N+-Ph is only 50-fold shorter lived in water compared to Ph-C≡N+-iPr (2); thus the effect of replacing an N-alkyl group with N-phenyl is modest. These two cations are also shown to have similar lifetimes to iminium analogs, e.g. Ph-CH=N+ (Me)-Ph. Thus, addition of water to analogous sp and sp2 hybridized systems occurs at a similar rate, and the increased steric access to the nitrilium plays at most a modest role. For the series where substituents in Ar′ were varied with Ar equal to phenyl, the Hammett plot for log kw correlated with σ, with ρ = - 1.4. For the series where Ar was varied, the data correlated much better with σ+, although ρ+ was only -0.6. This remarkably small effect of substituents in Ar constrasts with the effects seen in benzylic carbocations, but is consistent with the nitrilium structure, with most of the positive charge located on the nitrogen. Rate constant ratios kaz:kw, including the N-alkylnitrilium ion 2, are constant at ～104, with values of kaz well below the diffusion limit, even for the most reactive nitrilium ions. This is very different behaviour from that of carbocations and arylnitrenium ions of similar lifetimes in water. For these cations the rate constants kaz would be at or at least approaching the diffusion limit.

Syntheses and basicity of 4-(N,N-dimethylamino)-2-arylquinazolines

The reaction of substituted N-phenylbenzimidoyl chlorides with N,N-dimethylcyanamide in the presence of titanium tetrachloride has yielded seven 4-(N,N-dimethylamino)-2-arylquinazolines substituted on the phenyl ring with electron donating or withdrawing groups. pKa values have been determined for these compounds and analyzed in conjunction with the Hammertt σ constants to observe the influence of these phenyl substituents upon the basicity of 4-(N,N-dimemylamino)-2-arylquinazolines. The σ value, single crystal X-ray analysis and 15N-nmr spectra give evidence about the preferential site of protonation in such systems.