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Triphenylmethyl hexafluorophosphate

Triphenylmethyl hexafluorophosphate (also triphenylcarbenium hexafluorophosphate, trityl hexafluorophosphate, or tritylium hexafluorophosphate) is an organic salt with the formula , consisting of the triphenylcarbenium cation and the hexafluorophosphate anion .

Triphenylmethyl hexafluorophosphate is a brown powder that hydrolyzes readily to triphenylmethanol. It is used as a catalyst and reagent in organic syntheses.

Preparation

Triphenylmethyl hexafluorophosphate can be prepared by combining silver hexafluorophosphate with triphenylmethyl chloride:

:

A second method involves protonolysis of triphenylmethanol:

:

Structure and reactions

Triphenylmethyl hexafluorophosphate readily hydrolyzes, in a reaction that is the reverse of one of its syntheses:

:

Triphenylmethyl hexafluorophosphate has been used for abstracting hydride () from organic compounds. Treatment of metal-alkene and diene complexes one can generate allyl and pentadienyl complexes, respectively.

Triphenylmethyl perchlorate is a common substitute for triphenylmethyl hexafluorophosphate. However, the perchlorate is not used as widely, because, like other organic perchlorates, it is potentially explosive.

References

References

  1. {{PubChem. 2723954. Triphenylcarbenium hexafluorophosphate
  2. Urch, C.. (2001). "Encyclopedia of Reagents for Organic Synthesis".
  3. (1957). "Complex Fluorides. Part VIII.". Journal of the Chemical Society (Resumed).
  4. (1972). "Preparative Carbocation Chemistry; IV. Improved Preparation of Triphenylcarbenium (Trityl) Salts". Synthesis.
  5. (1994). "19F and 31P NMR Evidence for Silver Hexafluorophosphate Hydrolysis in Solution". Inorg. Chem..
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aromatic-compounds carbocations hexafluorophosphates phenyl-compounds
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