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2‐Arylimino(diferrocenyl)‐ and (di‐p‐anisyl)dihydropyrimidines: Novel Synthesis,Structures, and Electrochemistry
Authors:Elena I. Klimova  Eduardo A. Vázquez López  Marcos Flores Alamo  Luis A. Ortiz‐Frade  Gerardo Hernández‐Sánchez  Victor H. Sotelo Domínguez  Marcos Martínez García
Affiliation:1. Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, , Coyoacán, C.P., 04510 México D.F. México;2. Centro de Investigación y Desarrollo Tecnológico en Electroquímica S.C. Parque Tecnológico Querétaro, Pedro de Escobedo, , C.P., 76703 Querétaro, México;3. Universidad Nacional Autónoma de México, Instituto de Química, Cd. Universitaria, , Coyoacán, C.P., 04510 México D.F. México
Abstract:2,3‐Differocenyl‐ and 2,3‐dianisyl‐1‐methylsulfanylcyclopropenilium iodides react with 1,3‐diphenyl‐ and 1,3‐di‐o‐tolylguanidine to give 1‐aryl‐2‐arylimino‐5,6‐ ( 5a , 5b ) and ‐4,5‐diferrocenyl‐1,2‐dihydropyrimidines ( 6a , 6b ) (~ 2:1) and, respectively, 5,6‐ and 4,5‐dianisyl‐3‐phenyl‐2‐phenylimino‐1,2‐dihydropyrimidines (~ 2:1). Their structures were established based on the spectroscopic data and X‐ray diffraction analysis of 5,6‐diferrocenyl‐1‐(o‐tolyl)‐2‐(o‐tolyl)imino‐ and 4,5‐diferrocenyl‐1‐phenyl‐2‐phenylimino‐1,2‐dihydropyrimidines ( 5b and 6a , respectively). Electrochemical behavior of compounds 5b, 6b, and 5a+6a were investigated using experiments of cyclic voltammetry and chronoamperometry. For all the compounds, two electrochemical processes ( I , II ), attributed to the oxidations of the ferrocenes moieties were observed. The values of ΔE0′ ( II‐I ) and comproportionation constant Kcom are also reported. Additionally, an electrochemical oxidation with a fast coupled chemical reaction related to the pyrimide ring was also detected.
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