Hexaphenylcarbodiphosphorane

Hexaphenylcarbodiphosphorane is the organophosphorus compound with the formula C(PPh3)2 (where Ph = C6H5). It is a yellow, moisture-sensitive solid. The compound is classified as an ylide and as such carries significant negative charge on carbon. It is isoelectronic with bis(triphenylphosphine)iminium. The P-C-P angle is 131°.[1] The compound has attracted attention as an unusual ligand in organometallic chemistry.[2]

Hexaphenylcarbodiphosphorane
Names
Other names
bis(triphenylphosphoranylidene)methane
Identifiers
3D model (JSmol)
ChemSpider
Properties
C37H30P2
Molar mass 536.595 g·mol−1
Appearance yellow solid
Density 1.205 g/cm3
Melting point 198–201 °C (388–394 °F; 471–474 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation

The compound was originally prepared by deprotonation of the phosphonium salt [HC(PPh3)2]Br using potassium.[3]

An improved procedure entails production of the same double phosphonium salt from methylene bromide. The double deprotonation is effected with potassium amide.[4]

References

  1. Tonner, Ralf; Oexler, Florian; Neumueller, Bernhard; Petz, Wolfgang; Frenking, Gernot (2006). "Carbodiphosphoranes: The Chemistry of Divalent Carbon(0)". Angewandte Chemie International Edition. 45 (47): 8038–8042. doi:10.1002/anie.200602552. PMID 17075933.CS1 maint: uses authors parameter (link)
  2. Petz, W.; Frenking, G. (2010). Carbodiphosphoranes and Related Ligands. Top. Organomet. Chem. Topics in Organometallic Chemistry. 30. pp. 49–92. Bibcode:2010tmcn.book...49P. doi:10.1007/978-3-642-04722-0_3. ISBN 978-3-642-04721-3.CS1 maint: uses authors parameter (link)
  3. Ramirez, Fausto; Desai, N. B.; Hansen, B.; McKelvie, N. (1961). "Hexaphenylcarbodiphosphorane, (C6H5)3P:C:P(C6H5)3". Journal of the American Chemical Society. 83 (16): 3539–40. doi:10.1021/ja01477a052.CS1 maint: uses authors parameter (link)
  4. Gruber, Marco; Bauer, Walter; Maid, Harald; Schöll, Kilian; Tykwinski, Rik R. (2017). "Synthetic and NMR Studies on Hexaphenylcarbodiphosphorane (Ph3P=C=PPh3)". Inorganica Chimica Acta. 468: 152–158. doi:10.1016/j.ica.2017.04.018.
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