25751-79-5Relevant academic research and scientific papers
Synthesis tricyanovinyl derivatives via one-pot tandem reactions with heterogeneous catalyst Au@Cu(II)-MOF
Jin, Fa-Zheng,Chen, Chao-Qun,Zhao, Qun,Kan, Jing-Lan,Zhou, Yang,Chen, Gong-Jun
, p. 84 - 89 (2018/04/20)
In this article, the heterogeneous catalyst of Au@Cu(II)-MOF was prepared with high performance catalytic activities. By adding 5% mol Au@Cu(II)-MOF, the substrate of 2,6-di-tert-butylphenol (1) was oxidized to 2,6-di-tert-butyl-p-benzoquinone (2) with the yield of 99% using H2O2 as an oxidizing reagent. Moreover, treating the catalytic reaction mixture with malononitrile, one new product of 2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethane-1,1,2,-tricarbonitrile (3) was obtained with the isolated yield of 87%. However, in the absence of the catalyst of Au@Cu(II)-MOF, the intermedia of 2 and malononitrile react to form a product not 3 but its isomer 2-(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)ethane-1,1,2,-tricarbonitrile (4). At the meanwhile, in the presence of Au@Cu(II)-MOF and H2O2, the product of 3 with comparable isolated yield of 86% was isolated when 1 and malononitrile directly reacted during one pot tandem reaction. Furthermore, the tautomerization of 3 and 4 was also observed in CH2Cl2 solution driven by trimethylamine and acetic acid.
SYNTHESIS AND PROPERTIES OF 7,7-DIAMINOQUINONE METHIDES
Pavlickova, Libuse,Vasickova, Sona,Soucek, Milan
, p. 2675 - 2683 (2007/10/02)
Diaminoquinone methides Xa-Xe were prepared by aminolysis of the dicyanoquinone methide IX.From the isolated intermediates XI and XIII a four-step mechanism was deduced, involving addition and elimination steps in the order Ad-E-Ad-E.Condensation of N,N,N',N'-tetramethylchloroformamidinium chloride with 2,6-ditert-butylphenol afforded bis(dimethylamino)-quinone methide Xc which on transamination was converted to the diaminoquinone methides Xa and Xb.Analysis of physico-chemical data of diaminoquinone methides leads to the conclusion that their structure can be represented by the zwitterionic formula XVII rather than the quinonoid formula X.
