22230-43-9Relevant articles and documents
Extensive halogen scrambling and buttressing effects encountered upon treatment of oligobromoarenes with bases
Mongin, Florence,Marzi, Elena,Schlosser, Manfred
, p. 2771 - 2777 (2007/10/03)
As a rule, tri-, tetra- and pentahaloarenes readily undergo ortho-lithiation when treated with amide-type bases. However, halogen migration occurs whenever the substrate contains three or more contiguous halogen atoms, provided that at least one of them is bromine or iodine. Dismutation and reduction processes often take place concomitantly. In this manner, a variety of organometallic intermediates may be formed, the driving force always being a decrease in basicity. When no such energy gain can be achieved, a sterically crowded substrate may just turn out to be inert; this was found to be the case with 1,5-dibromo-3-fluoro-2-(trimethylsilyl)benzene, 1,5-dibromo-3-fluoro-2,4-bis(trimethylsilyl)benzene, and 1,5-dibromo-3-fluoro-2,4-diiodobenzene. Buttressing effects are apparently strong enough to prevent expedient deprotonation of those substrates.
POLYBROMO AROMATIC COMPOUNDS. I. SYNTHESIS OF SOME DERIVATIVES CONTAINING A PENTABROMOPHENYL RESIDUE
Tanaseichuk, B. S.,Rumyantseva, K. S.,Vasin, V. A.,Shishkin, V. N.,Rumyantsev, N. P.,et al.
, p. 1124 - 1128 (2007/10/02)
The synthesis of pentabromobenzyl bromide has been carried out, and its nucleophilic substitution reactions with alcohols, amines, sodium acetate, and silver nitrite have been studied.The C-Br bond in the bromomethyl group of pentabromobenzyl bromide readily undergoes homolysis, resulting in reductive dehalogenation.