Title: Olah's Reagent
CAS Registry Number: 62778-11-4
CAS Name: Hydrofluoric acid homopolymer compd with pyridine
Additional Names: pyridinium poly(hydrogen fluoride); PPHF
Line Formula: (C5H5N)x(HF)y
Literature References: Nucleophilic fluorinating agent; acts as a stabilized, less volatile form of hydrogen fluoride, q.v. Consists of approx 30% pyridine and 70% hydrogen fluoride (w/w) in equilibrium with a small amount of free hydrogen fluoride. Use in fluorination of steroids: C. G. Bergstrom et al., J. Org. Chem. 28, 2633 (1963). Prepn and use as an organic fluorinating reagent: G. A. Olah et al., Synthesis 1973, 779; idem et al., J. Org. Chem. 44, 3872 (1979). Peptide deprotection: S. Matsuura et al., J. Chem. Soc. Chem. Commun. 1976, 451. Review of use in organic synthesis: G. A. Olah et al., J. Fluorine Chem. 33, 377-396 (1986).
Properties: Liquid, stable to ~55°.
Use: Fluorinating reagent; deprotecting reagent in peptide chemistry. |