379266-13-4Relevant academic research and scientific papers
Evidence of reversibility in azo-coupling reactions between 1,3,5-tris(N,N-dialkylamino)benzenes and arenediazonium salts
Boga, Carla,Del Vecchio, Erminia,Forlani, Luciano,Tozzi, Silvia
, p. 8741 - 8747 (2007)
(Chemical Equation Presented) The reactions between strongly electron-rich aromatic substrates (1,3,5-tris(N,N-dialkylamino)benzenes, neutral carbon super nucleophiles) and diazonium salts produce moderately stable σ complexes (Wheland complexes). The reactivity of Wheland complexes with electrophiles (other diazonium salts, or 4,7-dinitrobenzofuroxan) produces exchange reactions in the electrophilic part: the better electrophile replaces the less powerful electrophile. In the same way, in Wheland complexes with the 1,3,5-tris(morpholinyl)-benzene, the 1,3,5-tris(piperidinyl)benzene replaces the less powerful nucleophile 1,3,5-tris(morpholinyl)-benzene. Evidence is reported here indicating that for the title system the reaction of the attack of the electrophilic reagent producing Wheland complexes is a reversible process. The final products of the diazo-coupling reactions undergo a further attack of some diazonium salts. From the final products of the double diazo-coupling reactions (diazo compounds), we collected evidence that is a clear instance of complete reversibility of the diazo-coupling reaction.
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
