92567-07-2

Upstream product

• 150935-09-4 C₈H₈N₃O⁽¹⁺⁾ 

Downstream Products

• 5470-34-8 4-methoxyformanilide 
• 123-11-5 4-methoxy-benzaldehyde 
• 874-90-8 4-methoxybenzonitrile 
• 150723-10-7 1-Methoxy-4-[(2,2,2-trifluoro-ethoxy)-(2,2,2-trifluoro-ethylsulfanyl)-methyl]-benzene 
• 1591950-66-1 methyl 3-azido-3-(4-methoxyphenyl)propanoate 
• 1591950-60-5 3-azido-3-(4-methoxyphenyl)-1-phenylpropan-1-one 
• 1591950-58-1 1-(1-azido-3-methylbut-3-en-1-yl)-4-methoxybenzene 
• 70978-37-9 1-(azidomethyl)-4-methoxybenzene 
• 150935-09-4 C₈H₈N₃O⁽¹⁺⁾ 
• 150723-08-3 1-[Azido-(2,2,2-trifluoro-ethylsulfanyl)-methyl]-4-methoxy-benzene 
• 150723-09-4 1-[Bis-(2,2,2-trifluoro-ethoxy)-methyl]-4-methoxy-benzene 

Relevant academic research and scientific papers

Spontaneous cleavage of gem-diazides: A comparison of the effects of α-azido and other electron-donating groups on the kinetic and thermodynamic stability of benzyl and alkyl carbocations in aqueous solution

The solvolysis reactions of ring-substituted benzylic and 1-propyl gem-diazides in water proceed by a stepwise mechanism through α-azido carbocation intermediates, which are captured by water to give the corresponding aldehyde as the sole detectable produ

The Effects of α-Substituents on the Kinetic and Thermodynamic Stability of 4-Methoxybenzyl Carbocations: Carbocation Lifetimes That Are Independent of Their Thermodynamic Stability

The following new rate constants for reaction of α-substituted 4-methoxybenzyl carbocations, 4-MeOC6H4CR1(R2)(1+), with a solvent of 50:50 (v/v) trifluoroethanol/water at 25 deg C and ionic strength 0.50 (NaClO4) are reported: 4-MeOC6H4CH(OMe)(1+), Ks = 2.2E7 s-1; 4-MeOC6H4CH(N3)(1+), ks = 3.3E5 s-1; 4-MeOC6H4C(CH3)2(1+), ks = 1.3E7 s-1; 4-MeOC6H4CH(CO2Et)(1+), ks = 1.4E7 s-1; 4-MeOC6H4CCH3(CF3)(1+), ks = 2.5E7 s-1.The values of ks for reaction of 4-MeOC6H4CR1(R2)(1+) with 50:50 (v/v) trifluoroethanol/water are nearly independent of very large changes in the thermodynamic stability of these carbocations caused by the addition of a wide range of electron-withdrawing or electron-donating groups at the α-position.In the most extreme case, the change from an α-methoxy to two α-(trifluoromethyl) substituents leads to a 23 kcal/mol thermodynamic destabilization of 4-MeOC6H4CR1(R2)(1+) relative to the neutral azide ion adducts but a 5-fold decrease in its reactivity toward solvent.The data show that the effects of α-substituents on the kinetic stability of 4-MeOC6H4CR1(R2)(1+) are complex and do not parallel the thermodynamic stability of these carbocations.The results are explained by consideration of the polar and resonance effects of the α-substituents on both the thermodynamic driving force and the intrinsic barrier for capture of the carbocations by solvent.These reactions are a new example of the consequences of the "principle of nonperfect synchronization".