Tautomeric equilibrium in trifluoroacetaldehyde arylhydrazones

作者: Agata Wojciechowska , Marcin Jasiński , Piotr Kaszyński

DOI: 10.1016/J.TET.2015.03.015

关键词:

摘要: A series of p-substituted phenylhydrazones trifluoroacetaldehyde (1) was synthesized and the azo-hydrazo (1–2) tautomeric equilibrium investigated experimentally using correlation analysis computationally with DFT methods. Investigation revealed strong impact substituent solvent polarity on ratio (1/2). Calculations also that acidity azo tautomers is similar to malonate esters.

参考文章(39)
Tautomerism : methods and theories Wiley-VCH Verlag GmbH & Co. KGaA. ,(2013) , 10.1002/9783527658824
Danièle Bonnet-Delpon, Jean-Pierre Bégué, Bioorganic and Medicinal Chemistry of Fluorine ,(2008)
Th. Zincke, H. Bindewald, Ueber Phenylhydrazinderivate des α- und β-Naphtochinons. Identität des α-Derivats mit dem Azoderivat des α-Naphtols Berichte der deutschen chemischen Gesellschaft. ,vol. 17, pp. 3026- 3033 ,(1884) , 10.1002/CBER.188401702282
Masanori Kawasaki, Hisashi Yamamoto, Catalytic Enantioselective Hetero-Diels-Alder Reactions of an Azo Compound Journal of the American Chemical Society. ,vol. 128, pp. 16482- 16483 ,(2006) , 10.1021/JA066726Y
Ho Yong Lee, Xinli Song, Hyunsoo Park, Mu-Hyun Baik, Dongwhan Lee, Torsionally responsive C3-symmetric azo dyes: azo-hydrazone tautomerism, conformational switching, and application for chemical sensing. Journal of the American Chemical Society. ,vol. 132, pp. 12133- 12144 ,(2010) , 10.1021/JA105121Z
Abel Ros, Elena Díez, Eugenia Marqués-López, Eloísa Martín-Zamora, Juan Vázquez, Javier Iglesias-Sigüenza, Rafael R. Pappalardo, Eleuterio Álvarez, José M. Lassaletta, Rosario Fernández, Experimental and theoretical studies on the asymmetric cyanosilylation of C2-symmetric hydrazones Tetrahedron-asymmetry. ,vol. 19, pp. 998- 1004 ,(2008) , 10.1016/J.TETASY.2008.03.020
Jia-Jie Wen, Hai-Tao Tang, Kai Xiong, Zong-Cang Ding, Zhuang-Ping Zhan, Synthesis of Polysubstituted Pyrazoles by a Platinum-Catalyzed Sigmatropic Rearrangement/Cyclization Cascade Organic Letters. ,vol. 16, pp. 5940- 5943 ,(2014) , 10.1021/OL502968C
Marcin Jasiński, Jason S. Gerding, Aleksandra Jankowiak, Krzysztof Gębicki, Jarosław Romański, Katarzyna Jastrzębska, Ajan Sivaramamoorthy, Kristein Mason, Donavan H. Evans, Małgorzata Celeda, Piotr Kaszyński, Functional Group Transformations in Derivatives of 6-Oxoverdazyl Journal of Organic Chemistry. ,vol. 78, pp. 7445- 7454 ,(2013) , 10.1021/JO400843Y