(Phenylethynyl)trimethylphosphonium bromide and bromoaurates(I)

Oliver Schuster, Hubert Schmidbaur

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

(Phenylethynyl)trimethylphosphonium bromide (1) has been reinvestigated by NMR spectroscopy and its crystal structure determined. In the monoclinic crystals, the cations are arranged in layers in the a-c planes, with their P-CsC-Ph axes parallel within one layer, but alternating in consecutive layers. The bromide anions are accommodated in channels between the cations. The spectroscopic and structural results are in agreement with the special reactivity pattern documented for ethynylphosphonium salts, in particular with the sensitivity to nucleophiles which e.g. prevents standard ylide formation. A slurry of polymeric phenylethynylgold [PhC≡CAu]n in dichloromethane reacts with [Me3PC=CPh]Br to give a clear solution of [Me3PC≡CPh]+ [PhC≡CAuBr]- (2). In a similar reaction, with soluble pentafluorophenylgold(tetrahydrothiophene), C6F5Au(IhI), the salt [Me3PC≡CPh] + [C6F5AuBr]- (3) is produced. All attempts to generate gold(I) complexes of the corresponding phosphonium ylide [Me2(PhC≡C)P≡CH2] by treatment of the two phosphonium salts (2,3) with strong base were not successful owing to side reactions induced by base.

Original languageEnglish
Pages (from-to)961-967
Number of pages7
JournalZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume61
Issue number8
DOIs
StatePublished - Aug 2006
Externally publishedYes

Keywords

  • Aurates(I)
  • Bromoaurates(I)
  • Ethynylphosphonium salts
  • Phosphonium Salts

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