The synthesis of 1,2-ethanediylbis(triphenylphosphonium) ditribromide as a new brominating agent in the presence of solvents and under solvent-free conditions

Crystal structure, characterization, Hirshfeld surface analysis and DFT studies of two [propane 3-bromo-1-(triphenyl phosphonium)] cations containing bromide (I) and tribromide (II) anions: The anion (II) as a new brominating agent for unsaturated compounds

“…The geometry of cation (bond lengths and angles) is general and comparable with our previously reported [27] The compound II crystallizes in the monoclinic system with P21/c space group with Z'=1, Z = 4. The asymmetric unit of this compound contains one propane 3-bromo-1-(triphenyl phosphonium) cation and one tribromide anion.…”

“…Tribromides are more suitable than the liquid bromine because of their crystalline nature, hence it makes it easier to store, transport, and maintain the desired stoichiometry. Instead of bromination with nonselective elemental bromine under harsh condition, organic phosphonium tribromides as well as ammonium and immidazolium tribromides were used to brominate the C-C double bonds and aromatic rings using mild conditions and in a selective manner [10,26,27]. The bromination of double bonds by liquid bromine or by tribromide salts has a different mechanisms, thermodynamics and kinetics.…”

“…[28]. [27], have all been used as mild brominating and oxidizing agents for the selective bromination of C-C multiple bonds and aromatic rings, these reactions are more favourable than using the very active, non-selective and toxic molecular bromine under harsh conditions. Reusability of tribromide salts is one of the interesting factors that predominate over molecular bromine as these salts can be used and recycled several times without any significant decrease in their performances.…”

Synthesis, crystal structure, Hirshfeld surface analysis, DFT calculations and characterization of 1,3-propanediylbis(triphenylphosphonium) monotribromide as brominating agent of double bonds and phenolic rings

“…Therefore several tribromides have been synthesized. The most frequently used quaternary phosphonium tribromide reagents as efficient brominating agents are benzyltriphenyl phosphonium tribromide 22,23 , tridecylmethyl phosphonium tribromide 21 , ethyltriphenyl phosphonium tribromide 24 , 1,2-ethanediylbis(triphenylphosphonium) ditribromide 25 and methyltriphenylphosphonim tribromide 26 .…”

Added catalyst-free, versatile and environment beneficial bromination of (hetero)aromatics using NBS in WEPA

“…However, majority of these procedures require added catalysts, oxidants, nonconventional solvents, reagents or large reaction times were occasionally operated at harsh conditions. Most recently, NBS/PhSSPh (or PhSSiMe 3 ) [19], NBS/indoles [20], NBS/hexafluoroisopropanol [21], NBS/I 2 [22], NaBr/ H 2 O 2 /AcOH [23] and 1,2-ethanediylbis(triphenylphosph onium)-ditribromide [24] were found attractive. Nevertheless, these also suffer with the necessity of catalysts, expensive solvents, oxidants or large reaction times.…”