This review describes the composition, preparation and applications in organic synthesis of polyphosphoric acid trimethylsilylester (PPSE). It covers the literature since it first appeared in the eighties until the first trimester of 2007. A discussion of the synthetic utility of PPSE, compared to other related reagents such as polyphosphoric acid (PPA) and polyphosphoric acid ethyl ester (PPE) as well as various Lewis acids, is also included.
ImamotoT., YokohamaH., and YokohamaM., Tetrahedron Lett., 1981, 22, 1803.
2.
ImamotoT., MatsumotoT., YokohamaH., YokohamaM., and YamaguchiK., J. Org. Chem., 1984, 49, 1105.
3.
YokohamaM., YoshidaS., and ImamotoT., Synthesis, 1982, 591. PPSE is now available from the Aldrich and Fluka companies under the name of trimethylsilyl polyphosphate.
A similar application to the synthesis of 1,3-disubstituted 1,4,5,6-tetrahydropyrimidines has also been described, see: OrelliL.R., NiemevzF., GarcíaM.V., and PerilloI.A., J. Heterocycl. Chem., 1999, 36, 105.
29.
HedreraM., and PerilloI.A., J. Heterocycl. Chem., 2000, 37, 1431.
30.
PerilloI., FernándezB., and LambanS., J. Chem. Soc., Perkin Trans. II, 1977, 2068.
31.
MarquartA.L., PodlogarR.L., HuberE.W., DemeterD.A., PeetN.P., WeintraubH.J.R., and AngelastroM., J. Org. Chem., 1994, 59, 2092.
32.
Phosphorus pentoxide (8%) in methanesulfonic acid: EatonP.E., CarlsonG.R., and LeeJ., J. Org. Chem., 1973, 38, 4071.
33.
CavaM.P., LakshmikanthamM.V., and MitchellM.J., J. Org. Chem., 1969, 34, 2665.
34.
HilmeyD.G., and PaquetteL.A., Org. Lett., 2005, 7, 2067.