Cascade Reactions Forming Highly Substituted, Conjugated Phospholes and 1,2-Oxaphospholes


  • The Swedish Research Council, the Göran Gustafsson Foundation, COST action 0802 PhoSciNet, and Uppsala University (U3MEC molecular electronics priority initiative) are all acknowledged for financial support.


original image

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.