Triphenylmethyl hexafluorophosphate explained

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.[1]

Preparation

Triphenylmethyl hexafluorophosphate can be prepared by combining silver hexafluorophosphate with triphenylmethyl chloride:[2]

A second method involves protonolysis of triphenylmethanol:[3]

Structure and reactions

Triphenylmethyl hexafluorophosphate readily hydrolyzes, in a reaction that is the reverse of one of its syntheses:[4]

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.[1]

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.[1]

See also

Notes and References

  1. Urch, C. . Triphenylmethyl Hexafluorophosphate . Encyclopedia of Reagents for Organic Synthesis . 2001 . 10.1002/047084289X.rt363f. 0471936235 .
  2. Sharp . D. W. A. . Sheppard . N. . Complex Fluorides. Part VIII. . Journal of the Chemical Society (Resumed) . 1957 . 674–682 . 10.1039/JR9570000674.
  3. Preparative Carbocation Chemistry; IV. Improved Preparation of Triphenylcarbenium (Trityl) Salts . Synthesis . 1972 . 10 . 544 . 1972 . Olah, G. . Svoboda, J. . Olah, J. . 10.1055/s-1972-21914.
  4. Fernandez-Galan, R. . Manzano, B . Otero, A . Lanfranchi, M . Pellinghelli, M. . 19F and 31P NMR Evidence for Silver Hexafluorophosphate Hydrolysis in Solution . Inorg. Chem. . 33 . 10 . 2309–2312 . 1994 . 10.1021/ic00088a039.