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Phosphatrioxa-adamantane

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Phosphatrioxa-adamantane
Names
Other names
1,3,5,7-tetramethyl-2,4,6-Trioxa-8-phosphatricyclo[3.3.1.13,7]decane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C10H17O3P/c1-7-5-9(3)13-8(2,11-7)6-10(4,12-7)14-9/h14H,5-6H2,1-4H3/t7-,8-,9+,10+/m1/s1
    Key: DSYQHWPNJZFRCU-IMSYWVGJSA-N
  • C[C@@]12C[C@]3(O[C@@](O1)(C[C@@](O2)(P3)C)C)C
Properties
C10H17O3P
Appearance white solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Phosphatrioxa-adamantane is an organophosphorus compound that is used as a precursor to bulky phosphine ligands.[1] Abbreviated CgPH (for cage phosphine), it is a white solid.

The compound is prepared by the condensation of two equivalents of acetylacetone and phosphine:

PH3 + 2 CH3C(O)CH2C(O)CH3 → HP(CH3CCH2CCH3)2O3 + H2O

The condensation is sometimes called the Buckler–Epstein reaction. Many diketones can be employed in place of acetylacetone. The P-H bond can be further derivatized, leading to a range of tertiary phosphines of potential value in homogeneous catalysis.

References

[edit]
  1. ^ Paul G. Pringle, Martin B. Smith "Phosphatrioxa-adamantane Ligands" in Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis, Edited by Paul C. J. Kamer and Piet W. N. M. van Leeuwen, 2012 John Wiley, New York. doi:10.1002/9781118299715.ch13