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TRISPHAT



TRISPHAT
IUPAC name Tetrabutylammonium Phosphorus(V) tris(tetrachlorocatecholate)PHAT
Other names Bu3NH+ PHAT-
Identifiers
CAS number 301687-57-0
Properties
Molecular formula [C16H36N][C18Cl12O6P]
Molar mass 1011.06
Appearance colourless solid
Solubility in water CH2Cl2
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Tributylammonium TRISPHAT is the an organic salt with the formula [(C4H9)3NH]+[P(O2C6Cl4)3-]. The anion features phosphorus(V) bonded to three tetrachlorocatecholate (C6Cl4O22-) ligands. This anion can be resolved into the enantiomers, which are optically stable (the picture shows the Δ enantiomer).

Additional recommended knowledge

The TRISPHAT anion has been used as a “chiral shift reagent” for cations. It improves the resolution of 1H NMR spectra by forming diastereomeric ion pairs.

Preparation

The anion is prepared by treatment of phosphorus pentachloride with tetrachlorocatechol followed by a tertiary amine gives the anion:

PCl5 + 3 C6Cl4(OH)2 → H[P(O2C6Cl4)3] + 5 HCl

H[P(O2C6Cl4)3] + Bu3N Bu3NH+ [P(O2C6Cl4)3]- Using a chiral amine, the anion can be readily resolved.[1]

References

  1. ^ F. Favarger, C. Goujon-Ginglinger, D. Monchaud, J. Lacour “Large-Scale Synthesis and Resolution of TRISPHAT [Tris(tetrachlorobenzenediolato) Phosphate(V)] Anion” Journal of Organic Chemistry, 2004, volume 69, pp. 8521 -8524, 2004. DOI: 10.1021/jo048641q.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "TRISPHAT". A list of authors is available in Wikipedia.
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