Bromination of 4,4′,4”-trisubstituted triphenylamines. Torsional control of electrophilic aromatic substitution was written by Kelley, William S.;Monack, Louise;Rogge, Peter T.;Schwartz, Robert N.;Varimbi, Suzanne P.;Walter, Robert I.. And the article was included in Justus Liebigs Annalen der Chemie in 1971.Recommanded Product: 615-55-4 This article mentions the following:
Bromination of (p-BrC6H4)3N, (p-MeC6H4)3N (I), and (p-MeOC6H4)3N (II) gave products with only one ortho-Br atom in each ring as determined by comparison of the NMR spectra with those of the appropriate 4-substituted 2-bromo- or 3-bromoanilines. D exchange in I and II took place in all 6 ortho positions. These reactions are interpreted as a result of a stepwise electrophilic substitution which occurs only when the aromatic ring undergoing reaction is rotated close to the fully activated conformation, in which it is coplanar with the three C-N bonds. The other two rings must be rotated far out of the plane to permit the ring undergoing substitution to attain this conformation. After bromination in one ortho position, the bulky Br atom prevents a return to the fully activated position whereas the smaller H or Cl do not. In the experiment, the researchers used many compounds, for example, 3,4-Dibromoaniline (cas: 615-55-4Recommanded Product: 615-55-4).
3,4-Dibromoaniline (cas: 615-55-4) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Recommanded Product: 615-55-4
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary