Change of mechanism with a change of substituents for a Zincke reaction

作者: Marcos Caroli Rezende , Ingrid Ponce , Rubén Oñate , Iriux Almodovar , Carolina Aliaga

DOI: 10.1016/J.TETLET.2014.03.136

关键词: Medicinal chemistryNucleophileZincke reactionElectron paramagnetic resonancePyridiniumChlorideChemistryPhotochemistryOrganic chemistryBiochemistryDrug discovery

摘要: The reaction between N-(2,4-dinitrophenyl)-4-(4-pyridyl)pyridinium chloride and 4-aminothiophenol led to an unexpected displacement of the 2,4-dinitrophenyl group, in contrast with …

参考文章(18)
Th. Zincke, G. Heuser, W. Möller, I. Ueber Dinitrophenylpyridiniumchlorid und dessen Umwandlungsproducte Justus Liebig's Annalen der Chemie. ,vol. 333, pp. 296- 345 ,(1904) , 10.1002/JLAC.19043330212
A.N. Kost, S.P. Gromov, R.S. Sagitullin, Pyridine ring nucleophilic recyclizations Tetrahedron. ,vol. 37, pp. 3423- 3454 ,(1981) , 10.1016/S0040-4020(01)98858-1
Julio Cezar Pastre, Carlos Roque D. Correia, Yves Génisson, Non-occurrence of a Zincke-like process upon treatment of 1-(2,4-dinitrophenyl)-3-methylimidazolium chloride with a chiral primary amine Green Chemistry. ,vol. 10, pp. 885- 889 ,(2008) , 10.1039/B804650F
E. C. Ashby, W. S. Park, A. B. Goel, Wei Yang Su, Single electron transfer in reactions of alkyl halides with lithium thiolates Journal of Organic Chemistry. ,vol. 50, pp. 5184- 5193 ,(1985) , 10.1021/JO00225A041
Ingrid Ponce, J. Francisco Silva, Ruben Oñate, Marcos Caroli Rezende, Maritza A. Páez, Jorge Pavez, José H. Zagal, Enhanced catalytic activity of Fe phthalocyanines linked to Au(111) via conjugated self-assembled monolayers of aromatic thiols for O2 reduction Electrochemistry Communications. ,vol. 13, pp. 1182- 1185 ,(2011) , 10.1016/J.ELECOM.2011.08.050
Dirk Bongard, Martin Möller, S. Nagaraja Rao, David Corr, Lorenz Walder, Synthesis of Nonsymmetrically N,N′-Diaryl-Substituted 4,4′-Bipyridinium Salts with Redox-Tunable and Titanium Dioxide (TiO2)-Anchoring Properties Helvetica Chimica Acta. ,vol. 88, pp. 3200- 3209 ,(2005) , 10.1002/HLCA.200590257
N. O. Mahmoodi, M. Mamaghani, A. Ghanadzadeh, M. Arvand, M. Fesanghari, Photochromic behavior of several new synthesized dyes via Zincke salts Journal of Physical Organic Chemistry. ,vol. 23, pp. 266- 270 ,(2009) , 10.1002/POC.1623
Wei-Chieh Cheng, Mark J. Kurth, THE ZINCKE REACTION. A REVIEW Organic Preparations and Procedures International. ,vol. 34, pp. 585- 608 ,(2002) , 10.1080/00304940209355784