22230-46-2Relevant academic research and scientific papers
Superelectrophilic bromination of deactivated aromatic rings with tribromoisocyanuric acid-an experimental and DFT study
de Almeida, Leonardo S.,Esteves, Pierre M.,de Mattos, Marcio C.S.
experimental part, p. 3001 - 3004 (2009/09/28)
The reaction of deactivated arenes with tribromoisocyanuric acid (TBCA) in 98% H2SO4 produced bromoarenes in good yields. The acidity of the medium controls the strength of the brominating agent and the amount of polybrominated products. DFT calculations at B3LYP/6-311++G** level showed that the protonated TBCA (a superelectrophilic species) can easily transfer Br+ to deactivated arenes, in order to decrease internal charge-charge repulsion.
Thermal Stability Studies on a Homologous Series of Nitroarenes
Oxley, Jimmie C.,Smith, James L.,Ye, Hong,McKenney, Robert L.,Bolduc, Paul R.
, p. 9593 - 9602 (2007/10/02)
The thermal stabilities of a number of nitroarenes were examined in solution and in condensed phase.In general, increasing the number of nitro groups decreased thermal stability.Changing the substituent on 1-X-2,4,6-trinitrobenzene from X = H to NH2 to CH3 to OH accelerated decomposition; this effect was attributed to increased ease of intramolecular proton transfer to an ortho nitro group, thus weakening the carbon-nitrogen bond.In solution, the effect of increasing substitution from n = 1 to n = 3 on Xn(NO2)3C6H3-n was uniformly that of decreasing the thermal stability of the species.However, in condensed phase, results suggested that crystal habit may be more important than molecular structure; for X = Br, CH3, and NH2, the more substituted species was the more stable.
BROMINATION OF DEACTIVATED AROMATIC COMPOUNDS
Andrievskii, A.M.,Gorelik, M.V.,Avidon, S.V.,Al'tman, E.Sh.
, p. 1519 - 1524 (2007/10/02)
Unreactive aromatic compounds can be brominated with high yields by the action of bromine and nitric acid or another oxidizing agent (iodic acid, hydrogen peroxide, etc.) in concentrated sulfuric acid or oleum.Bromination in the presence of nitric acid has lower substrate selectivity than the concurrent nitration.Moderately deactivated aromatic substrates are nitrated initially, whereas inactive substrates are brominated.It is suggested that the electrophilic brominating agent is sulfohypobromite in the form of a complex with sulfuric acid.
POLYBROMINATED AROMATIC COMPOUNDS VI. EXHAUSTIVE BROMINATION IN THE RING OF DEACTIVATED AROMATIC COMPOUNDS
Shishkin, V.N.,Bolusheva, I.Yu.,Lapin, K.K.,Tanaseichuk, B.S.
, p. 1303 - 1308 (2007/10/02)
A convenient method is developed for the synthesis of perbrominated aromatic compounds containing electronegative groups (NO2, CN, COOH) by exhaustive bromination of the starting compounds with bromine in concentrated sulfuric acid in oleum in the presence of mecuric oxide at 35-60 deg C.
