Stepwise Reduction of an -Phosphonio-Carbocation to a Crystalline Phosphorus Radical Cation and an Acridinyl-Phosphorus Ylide. Academic Article uri icon

abstract

  • We have synthesized the dicationic -phosphonio-carbocation 1(2+) , which can be regarded as a two-electron oxidized phosphorus ylide. Carbocation 1(2+) exhibits two reversible reduction waves at -0.28 and -0.90V (vs. Fc(+) /Fc) indicating that both the radical cation 1(.+) and the neural phosphorus ylide 1 can be generated. Indeed, reduction of 1(2+) with Zn afforded 1(.+) as a dark green solid that was characterized by XRD and EPR spectroscopy, and reduction with Mg(Ant)(THF)3 gave 1, which was characterized by (1) H and (31) PNMR spectroscopy. Computational analyses reveal the stepwise population of a C-P bonding orbital upon reduction of 1(2+) .

published proceedings

  • Chemistry

altmetric score

  • 1

author list (cited authors)

  • Hudnall, T. W., Dorsey, C. L., Jones, J. S., & Gabbai, F. P.

citation count

  • 12

complete list of authors

  • Hudnall, Todd W||Dorsey, Christopher L||Jones, James S||Gabbaiï, François P

publication date

  • February 2016

publisher