4650. Hendrickson's Reagent
Nomenclature
CAS number: 72450-51-2
μ-Oxohexaphenyldiphosphorus(2+) salt with trifluoromethanesulfonic
acid (1:2); triphenylphosphonium anhydride trifluoromethanesulfonate; POP. C36H30OP2.2CF3O3S; mol wt 838.71.
C 54.42%, H 3.61%, O 13.35%, P 7.39%, F 13.59%, S 7.65%.
Description and 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).
