81090-52-0Relevant academic research and scientific papers
Nitromethane with IBX/TBAF as a nitrosating agent: Synthesis of nitrosamines from secondary or tertiary amines under mild conditions
Potturi, Hima K.,Gurung, Ras K.,Hou, Yuqing
, p. 626 - 631 (2012/02/16)
Aliphatic or aromatic N,N-disubstituted nitrosamine was generated in fair to excellent yield from the reaction of a secondary or tertiary amine with o-iodoxybenzoic acid (IBX) or o-iodosylbenzoic acid (IBA)/R4NX (X = halide) and nitromethane. The product yield was strongly influenced by both the halide of R4NX and iodanes. IBX gave a higher yield than IBA, while the halides follow F- > Cl- > Br- ～ I-. Nitrous acid formed in situ from nitromethane and IBX (or IBA)/halides is likely responsible for the observed reaction.
Bromation regioselective en serie aromatique. I: Monobromation en position para de phenols et d'amines aromatiques par le tribromure de tetrabutylammonium
Berthelot, Jacques,Guette, Catherine,Desbene, Paul-Louis,Basselier, Jean-Jacques,Chaquin, Patrick,Masure, Daniel
, p. 2061 - 2066 (2007/10/02)
The reaction of tetrabutylammonium tribromide (TBABr3) with phenols and aromatic amines in aprotic and non-basic solvents at 20 deg C gives exclusively the corresponding para-brominated compounds in high yields.A mechanism involving electrophilic substitution by the tribromide anion Br3- itself is suggested to account for the results, especially the regioselective para bromination.Key words: bromination, tetrabutylammonium tribromide, phenols, aromatic amines.
REGIOSELECTIVE MONOBROMINATION OF AROMATIC AMINES WITH TETRABUTYLAMMONIUM TRIBROMIDE
Berthelot, J.,Guette, C.,Essayegh, M.,Desbene, P.L.,Basselier, J.J.
, p. 1641 - 1646 (2007/10/02)
A simple and efficient method for monobromination of aromatic amines predominantly in the para position is reported.Tetrabutylammonium tribromide is used at 20 deg C and yields of parabromoanilines are higher than 90percent.
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.
