Photochemical and Photophysical Behavior of 2-halo-N,N-Diphenylaniline in Photostimulated Intramolecular Arylation Reactions. Synthesis of Carbazoles

MICAELA D. HEREDIA; MARÍA E. BUDÉN; JAVIER I. BARDAGÍ; MARCELO PUIATTI; ROBERTO A. ROSSI

Villa Carlos Paz

Congreso; ELAFOT XIII; 2017

Our proposal is to investigate the mechanism of these photosubstitution reactions supplying information from the study of experimental reaction conditions, photophysical properties ((UV-Vis, steady state fluorescence and time-resolved fluorescence) and computational data. Under this super-basic conditions, dimsyl anion is formed from a strong base (KOtBu) and DMSO (solvent). Some initially results reveal that no Charge Transfer Complex (CTC) interaction could be detected by the UV-Vis absorption spectrum between the dimsyl anion and triarylamines. Furthermore, dimsyl anion is responsible for inducing the initiation by a photo-BHAS process on alkyl and arylhalides. There was not change fluorescence intensity of 2-clhorotriarylamine increasing concentrations of KOtBu, however a new maxima of the emission spectra was detected. In this work, a complete mechanistic picture of this cyclization reaction will be discussed.