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

Reihaneh Salmasi, Mostafa Gholizadeh, Alireza Salimi, Jered C. Garrison

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Abstract: 1,2-Ethanediylbis(triphenylphosphonium) ditribromide was quantitatively prepared and used for the bromination of anilines and phenols in the presence of a mixed solvent system (DCM/MeOH 2:1) and also under solvent-free conditions. This new ionic liquid has advantages over similar brominating agents in terms of short reaction time, simple workup, regioselectivity and high yields. Single-crystal X-ray analysis of title salt revealed that the bistriphenylphosphonium cation is organized around an inversion center located at the center of the –CH2–CH2– bridge and the two triphenylphosphine segments are anti with respect to one another. All the tribromide anions adopt a linear geometry with different Br–Br–Br bond angles for each anion. Graphical Abstract: [Figure not available: see fulltext.]

Original languageEnglish (US)
Pages (from-to)2019-2028
Number of pages10
JournalJournal of the Iranian Chemical Society
Volume13
Issue number11
DOIs
StatePublished - Nov 1 2016

Keywords

  • Bromination
  • Crystal structure
  • Nucleophilic substitutions
  • Regioselectivity
  • Solvent-free

ASJC Scopus subject areas

  • Chemistry(all)

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