84751-99-5Relevant academic research and scientific papers
Aryl C-H amination initiated by laccase-mediated oxidation of 4-phenylurazole
Chen, Yu-Jue,Zhang, Guo-Yan,He, Yan-Hong,Guan, Zhi
, p. 4216 - 4221 (2019)
A mild amination of aryl C-H has been developed using laccase as a green and sustainable catalyst, aerial O2 as the oxidant, with water being the only by-product. Various aromatic compounds including anilines, naphthols, quinolines and substituted benzenes can be aminated with 4-phenylurazole in yields up to 93%.
Interaction of Electron-Deficient 1,2,4-Triazoline-3,5-diones with Electron-Rich Polyalkoxybenzenes
Hall, J. Herbert
, p. 1708 - 1712 (2007/10/02)
4-Substituted-1,2,4-triazoline-3,5-diones have been found to form charge-transfer complexes with 1,3,5-trimethoxybenzene, 1,3-dimethoxybenzene, and 1,4-dimethoxybenzene but not with anisole.In the cases of 1,3,5-trimethoxybenzene and 1,3-dimethoxybenzene a reaction occurs to give aromatic substitution; the relative rates are 1,3,5-trimethoxybenzene >1,3-dimethoxybenzene >1,4-dimethoxybenzene.The rate of reaction of 4-butyl-1,2,4-triazoline-3,5-dione (n-BuTAD) with 1,3,5-trimethoxybenzene (TMB) increases with decreasing temperature to give apparent activation parameters: ΔH* = -5.9 kcal/mol, ΔS* = -78 cal deg-1 mol-1.The rate is also dependent on the length of time that solutions of the n-BuTAD are exposed to ambient light, suggesting involvement of the urazolyl radical.It is suggested that the overall rate expression is - = k1Keq(n-BuTAD)(TMB)(Ur.), where (Ur.) is the urazolyl radical concentration, Keq is the equilibrium constant for charge-transfer complex formation, and k1 is the rate constant for attack of Ur. on the charge-transfer complex.
