Formation and characterization of zwitterionic stereoisomers from the reaction of B(C6F5)3 and NEt2Ph: (E)- and (Z)-[EtPhN+=CHCH2-B- (C6F5)3]

Nicolas Millot, Catherine C. Santini*, Bernard Fenet, Jean Marie Basset

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

77 Scopus citations

Abstract

The stoichiometric reaction of B(C6F5)3 and NEt2Ph I, at room temperature, in an aromatic solvent, has been investigated by 1D and 2D NMR spectroscopy (1H, 11B, 13C, 15N and 19F). No Et2PhN·B(C6F5)3 adduct was observed. An equilibrium between free B(C6F5)3, NEt2Ph, [HB(C6F5)3]-(HNEt2Ph) + and two zwitterionic stereoisomers (E)- and (Z)-[EtPhN+=CH-CH2-B-(C6 F5)3] (30%) in an E/Z ratio of 3:2 was observed. Whatever the protic reagent Z-OH [Z = H, SiPh3, (c-C5H9)7O12Si8, or silanol group of silica], all the equilibria involved in solutions of I are quantitatively displaced towards the ionic form [Z-O-B(C6F5)3]-(HNEt2 Ph)+. In the case of dimethylaniline, besides free B(C6F5)3 and Me2NPh, the 1:1 adduct (C6F5)3B·NMe2Ph and an iminium salt [PhCH3N= CH2]+[HB(C6F5)3] - have been identified.

Original languageEnglish (US)
Pages (from-to)3328-3335
Number of pages8
JournalEuropean Journal of Inorganic Chemistry
Issue number12
DOIs
StatePublished - Dec 1 2002

Keywords

  • Aniline
  • Boranes
  • NMR spectroscopy
  • Zwitterions

ASJC Scopus subject areas

  • Inorganic Chemistry

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