608-90-2Relevant articles and documents
Polybromoaromatic compounds: X. Reactions of polybromobenzenes with primary and secondary amines
Shishkin,Esina,Lapin,Butin
, p. 374 - 377 (2007/10/03)
Polybromobenzenes C6Br5X (X = Br, F, CN, NO 2) react with primary amines (methylamine and cyclohexylamine) to give nucleophilic substitution products; reactions of the same substrates with secondary amines (dimethylamine, diethylamine, piperidine, and morpholine) are accompanied by hydrodebromination processes.
PERBROMINATION OF BENZENE AND SOME OF ITS DERIVATIVES
Golounin, A. V.,Shukhta, T. K.,Kirienko, E. K.,Petrova, M. P.,Esavkin, E. V.
, p. 1167 - 1169 (2007/10/02)
Perbrominated compounds - pentabromophenol, hexabromobenzene, pentabromotoluene, polychlorobromobenzenes, and decabromodiphenyl ether - have been obtained.Substitution bromination has been discovered in treating diphenyl sulfoxide, diphenyl sulfide, diphenylmethane, diphenyl oxide, and benzophenone with excess bromine in the presence of AlBr3.A series of ethers and esters of pentabromophenol have been obtained; their hydrolysis has been carried out.A negative influence of ferric halides has been discovered in exhaustive bromination of aromatic compounds.
Nucleophilic Displacement in Polyhalogenoaromatic Compounds. Part 11. Kinetics of Protiodeiodination of Iodoarenes in Dimethyl Sulphoxide-Methanol
Bolton, Roger,Moore, Clive,Sandall, John P.B.
, p. 1593 - 1598 (2007/10/02)
The rates of methoxide-ion induced protiodeiodination of a number of polychloroiodobenzenes and their derivatives have been measured in dimethyl sulphoxide-methanol (9:1 v/v; 323.2 K).The true reagent under these conditions appears to be the dimethyl sulphoxide anion, and the rates of reaction in some cases appear to approach that expected of a diffusion controlled process.This corresponds to a major decrease in the efficacy of further activating substituents in the aromatic system, altough deactivating groups such as p-OMe still show large effects.Chlorine promotes protiodeiodination in the order of efficiency o-Cl > m-Cl > p-Cl; the trifluoromethyl group activates displacement in the order o-CF3 > p-CF3 > m-CF3, although with much less difference between isomeric sites. o-Nitro-groups promote protiodeiodination whereas the p-nitro-group encourages methoxydeiodination.No evidence of methoxydeiodination was found in attack of the polychloroiodobenzenes, although the rates of methoxydechlorination of the corresponding polychlorobenzenes suggest that in some cases this might occur.Evidence rejecting the possible SRN1 mechanism and supporting nucleophilic attack by a carbanionic species upon iodine is presented.
