16857-93-5Relevant academic research and scientific papers
Evidence for carbon-carbon meisenheimer-wheland complexes between superelectrophilic and supernucleophilic carbon reagents
Boga, Carla,Del Vecchio, Erminia,Forlani, Luciano,Mazzanti, Andrea,Todesco, Paolo E.
, p. 3285 - 3289 (2005)
(Chemical Equation Presented) Proposal accepted: NMR experiments have shown unequivocally that the previously only proposed zwitterionic carbon-carbon Meisenheimer-Wheland complexes are formed in the reaction of 4,6-dinitrobenzofuroxan (DNBF) with 1,3,5-tris(N,N-dialkylamino)benzenes. Increasing the temperature results in a rapid exchange between three homomeric forms of the complex (see scheme; NR2 = piperidyl, morpholinyl, pyrrolidinyl).
Quantification of the Lewis Basicities and Nucleophilicities of 1,3,5-Tris(dialkylamino)benzenes
Micheletti, Gabriele,Mayer, Robert J.,Cino, Silvia,Boga, Carla,Mazzanti, Andrea,Ofial, Armin R.,Mayr, Herbert
, p. 6347 - 6357 (2021)
Equilibrium constants for the formation of Wheland complexes from 1,3,5-tris(dialkylamino)benzenes and benzhydrylium ions (Ar2CH+) have been determined photometrically in dichloromethane solution at 20 °C. The Lewis basicity of the r
Nickel-catalysed sequential amination of aryl- and heteroaryl di- and trichlorides
Desmarets, Christophe,Schneider, Rapha?l,Fort, Yves
, p. 7657 - 7664 (2007/10/03)
Unsymmetrical 1,3-diaminobenzenes and diaminopyridines were efficiently prepared by reaction of 3-chloroanilines and chloroaminopyridines with amines via a nickel-catalysed amination. The Ni/2,2′-bipyridine catalyst is also effective for the sequential am
Aminobenzenes, 21. - Electron Transfer in the Reactions of Halogeno ?-complexes of 1,3,5-Tris(1-pyrrolidinyl)benzene with Nucleophiles
Effenberger, Franz,Baeuerle, Peter,Seufert, Walter,Stohrer, Wolf-Dieter
, p. 193 - 200 (2007/10/02)
Iodo, bromo, chloro , and thiocyanato ?-complexes 4, accessible as crystalline compounds from 1,3,5-tris(1-pyrrolidinyl)benzene (1) with halogens and dirhodan, respectively, react with nucleophiles or bases under dehalogenation, deprotonation, dimerization, or H ?-complex formation.The product formation depends on the redox potentials of the ?-complexes ( acceptors) and the nucleophiles ( donors) , on the leaving tendency of the substituents on C-1 of the ?-complexes, and on the reaction time.The unexpected reactions are interpreted by an electron transfer from the nucleophile Y to the ?-complex A+ to give the radical A., a subsequent heterolytic dissociation to the 1,3,5-tris(1-pyrrolidinyl)benzene radical cation C+., and its follow-up reactions (addition of nucleophiles, dimerization, and H abstaction).The H ?-complex 6 results as the most stable final product after long reaction times because of its lowest acceptor properties and poor nucleofugal leaving tendency of a hydride ion.
