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Triphenylmethyl hexafluorophosphate
Chemical compound From Wikipedia, the free encyclopedia
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Triphenylmethyl hexafluorophosphate (also triphenylcarbenium hexafluorophosphate, trityl hexafluorophosphate, or tritylium hexafluorophosphate) is an organic salt with the formula [(C6H5)3C]+[PF6]−, consisting of the triphenylcarbenium cation [(C6H5)3C]+ and the hexafluorophosphate anion [PF6]−.[1]
Triphenylmethyl hexafluorophosphate is a brown powder that hydrolyzes readily to triphenylmethanol. It is used as a catalyst and reagent in organic syntheses.[2]
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Preparation
Triphenylmethyl hexafluorophosphate can be prepared by combining silver hexafluorophosphate with triphenylmethyl chloride:[3]
- Ag+[PF6]− + (C6H5)3CCl → [(C6H5)3C]+[PF6]− + AgCl
A second method involves protonolysis of triphenylmethanol:[4]
- H[PF6] + (C6H5)3COH → [(C6H5)3C]+[PF6]− + H2O
Structure and reactions
Triphenylmethyl hexafluorophosphate readily hydrolyzes, in a reaction that is the reverse of one of its syntheses:[5]
- [(C6H5)3C]+[PF6]− + H2O → (C6H5)3COH + H[PF6]
Triphenylmethyl hexafluorophosphate has been used for abstracting hydride (H−
) from organic compounds. Treatment of metal-alkene and diene complexes one can generate allyl and pentadienyl complexes, respectively.[2]
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.[2]
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See also
References
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