Singlet (Phosphino)phosphinidenes are Electrophilic

J Am Chem Soc. 2016 Jul 13;138(27):8356-9. doi: 10.1021/jacs.6b04232. Epub 2016 Jun 30.

Abstract

A room-temperature stable (phosphino)-phosphinidene reacts with carbon monoxide, stable singlet carbenes, including the poor π-accepting imidazol-2-ylidene, and phosphines giving rise to the corresponding phosphaketene, phosphinidene-carbene and phosphinidene-phosphine adducts, respectively. Whereas the electronic ground-state calculations indicate a PP multiple bond character in which the terminal phosphorus is negatively charged, the observed reactivity clearly indicates that (phosphino)phosphinidenes are electrophilic as expected for an electron-deficient species. This is further demonstrated by competition experiments as well as by the results of Fukui function calculations.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.