Hendrickson's Reagent
Title: Hendrickson's Reagent
CAS Registry Number: 72450-51-2
CAS Name: m-Oxohexaphenyldiphosphorus(2+) salt with trifluoromethanesulfonic acid (1:2)
Additional Names: triphenylphosphonium anhydride trifluoromethanesulfonate; POP
Molecular Formula: C36H30OP2.2CF3O3S
Molecular Weight: 838.71
Percent Composition: C 54.42%, H 3.61%, O 13.35%, P 7.39%, F 13.59%, S 7.65%
Literature References: Alternative to Mitsunobu reagents for the esterification of primary alcohols. Synthesis method: J. B. Hendrickson, S. M. Schwartzman, Tetrahedron Lett. 16, 277 (1975). Prepn: A. Aaberb et al., ibid. 20, 2263 (1979). Synthetic applications as a dehydration agent: J. B. Hendrickson, Md. S. Hussoin, J. Org. Chem. 52, 4137 (1987); eidem et al., Synlett 1996, 661; and X-ray crystal structure determn: S.-L. You et al., Angew. Chem. Int. Ed. 42, 83 (2003). Mechanism of dehydration reactions vs the Mitsunobu reaction: K. E. Elson et al., Org. Biomol. Chem. 1, 2958 (2003).
Properties: White crystalline solid, mp 74-75°. Sol in pyridine, THF. Water and air sensitive.
Melting point: mp 74-75°
Use: Dehydration reagent in organic synthesis.

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