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Keywords:

  • acetylenes;
  • conjugation;
  • cumulenes;
  • phospha-Wittig;
  • reaction mechanisms
Thumbnail image of graphical abstract

More than just a carbon copy: The reaction of a phospha-Wittig–Horner reagent with diacetylenic ketones (see scheme) results in a cascade of reactions that can lead to both an oxaphosphole-terminated cumulene system and an alkene-bridged bis-phosphole. The reaction outcome is determined by the nature of the acetylene termini, with phenyl groups stabilizing a carbene intermediate that dimerizes to give the bis-phosphole product.