20442-80-2Relevant academic research and scientific papers
Aminobenzenes, XVII. Addition Products of N,N-Dialkylanilines and Bromine - Synthesis and Reactions
Effenberger, Franz,Steinbach, Adalbert,Epple, Gerhard,Hanauer, Johann
, p. 3539 - 3551 (2007/10/02)
4-Bromo-N,N-dialkylanilines 1 react with bromine in inert solvents to give the 1:1 addition compounds 2 or 3.IR and UV investigations established the structure of the isolated products to be CT complexes (? complexes) for 2 and N-bromoanilinium bromides for 3.The adducts 2 react to yield substitution products 6 and dealkylation products 7 in polar solvents (dimethylformamide, acetic acid, methanol), whereas the main product from 2a by reaction in acetone is N,N,N',N'-tetramethylbenzidine (9).Radical cations 10 are postulated to be the determining intermediates for these reactions.The tendency of the alkyl groups to be cleaved off decreases in the order isopropyl > ethyl > methyl.Under analogous conditions the N-bromo compounds 3 give predominantly the anilines 1 and only small amounts of substitution products 6, dealkylation and reaction to benzidines were not observed.
