Phosphatrioxa-adamantane

Phosphatrioxa-adamantane
Names
	Other names 1,3,5,7-tetramethyl-2,4,6-Trioxa-8-phosphatricyclo[3.3.1.13,7]decane
Identifiers
CAS Number	26088-25-5;
3D model (JSmol)	Interactive image;
ChemSpider	59759745;
PubChem CID	102407854; 22121380;
	InChI 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;
	SMILES C[C@@]12C[C@]3(O[C@@](O1)(C[C@@](O2)(P3)C)C)C;
Properties
Chemical formula	C10H17O3P
Appearance	white solid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

^ 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

[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

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