Naphthalene-1,8-diyl Bis(Halogenophosphanes): Novel Syntheses and Structures of Useful Synthetic Building Blocks

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A series of new bay region disphospha-functionalised naphthalenes is reported. The reduction of ylidic phosphonium phosphoride NapP(2)Cl(6) (1) (Nap = naphthalene-1,8-diyl) with MeOPCl2 gives the important synthon Nap(PCl2)(2) (2) in nearly quantitative yield. Reaction of I with magnesium metal affords (NapP(2))(n) (3), which reacts with Br-2 and I-2 yielding Nap(PBr2)(2) (4) and Nap(PI)(2) (5), respectively. X-ray structure determinations reveal a twisted geometry of the naphthalene ring in sterically strained 2 and 4, whilst the presence of a P-P bond in 5 results in the release of the steric strain and generation of the planar NapP(2) moiety. Although the tetrahedral P environments are severely distorted the sigma(3)P-sigma(3)P bonding in 5 represents a new type of P-P bonding environment in 1,8-diphosphanaphthalenes. Compounds 1, 4 and 5 each represent the highest coordination, achievable by direct halogenation. The new compounds 2-5 were fully characterised by NMR, IR, and Raman spectroscopy, mass spectrometry, and elemental analysis.

Original languageEnglish
Pages (from-to)215-222
Number of pages8
JournalChemistry - A European Journal
Issue number1
Publication statusPublished - 3 Jan 2003


  • halogens
  • neighboring-group effects
  • phosphorus
  • strained molecules


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