TRISPHAT

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Template:Chembox TRISPHAT (full name tris(tetrachlorocatecholato)phosphate(1−)) is an inorganic anion with the formula Template:Chem/link often prepared as the tributylammonium (Template:Chem/link) or tetrabutylammonium (Template:Chem/link salt. The anion features phosphorus(V) bonded to three tetrachlorocatecholate (Template:Chem/link) ligands. This anion can be resolved into the axially chiral enantiomers, which are optically stable (the picture shows the Δ enantiomer).

The TRISPHAT anion has been used as a chiral shift reagent for cations.[1] 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.[2]

References

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