TRISPHAT
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| TRISPHAT | |
|---|---|
 |
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| 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 |
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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).
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.
[edit] 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]
[edit] References
- ^ 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.
