TRISPHAT

TRISPHAT
Names
IUPAC name
Tetrabutylammonium Phosphorus(V) tris(tetrachlorocatecholate)PHAT
Other names
Bu3NH+ PHAT
Identifiers
301687-57-0 YesY
ECHA InfoCard 100.164.647
Properties
[C16H36N][C18Cl12O6P]
Molar mass 1011.06
Appearance colourless solid
CH2Cl2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Tributylammonium TRISPHAT is 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).

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 issued from Wikipedia - version of the 6/21/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.