Benzyltriphenylphosphonium and n-butyltriphenylphosphonium peroxodisulfates are stable and easily prepared oxidising agents. These reagents are able to convert different thioamides and thioureas to their oxygen analogues in good to excellent yields. Thiono esters are also transformed to esters in high yields. Thioketones such as thiobenzophenone and thiofluorenone are converted to their ketones in high yields while, 4-nitrothiobenzophenone, 2-aminothiobenzophenone and 4-chlorothiobenzophenone remained intact in the reaction mixture.
(a) BartonD., OllisW. D., and JonesD. N., Comprehensive Organic Chemistry. The Synthesis and Reactions of Organic Compounds, Pergamon Press, Oxford, 1979, Vol. 3, Part II, pp. 3–487; (b) E. Schaumann, B. M. Trost, I. Fleming and E. Winterfeldt, Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991, Vol. 6, pp. 419-434.
2.
CappsH.H., and DehnW. M., J. Am. Chem. Soc., 1932, 54, 4301.
3.
MikolajczykM., and LuczakJ., J. Org. Chem., 1978, 43, 2132.
LeyS.V., MeerholzC. A., and BartonD. H. R., Tetrahedron Lett., 1980, 21, 1785.
17.
ChalaisS., CornelisA., LaszloP., and MathyA., Tetrahedron Lett, 1985, 26, 2327.
18.
JorgensenK.A., El-WassimyM. T. M., and LawessonS.-O., Tetrahedron, 1983, 39, 469.
19.
RavindranathanT., ChavanS. P., AwachatM. M., and KelkarS. V., Tetrahedron Lett, 1995, 36, 2277.
20.
KimY.H., ChungB. C., and ChangH. S., Tetrahedron Lett, 1985, 26, 1079.
21.
VarmaR.S., and KumarD., Synth. Commun., 1999, 29, 1333.
22.
MavassaghB., LakourajM. M., and GhodratiK., Synth. Commun., 2000, 30, 2353.
23.
Mohammadpoor-BaltorkI., HajipourA. R., and MohammadiH., Bull. Chem. Soc. Jpn., 1998, 71, 1649.
24.
Mohammadpoor-BaltorkI., HajipourA. R., and HaddadiR., J. Chem. Res. (S), 1999, 102.
25.
TajbakhshM., Mohammadpoor-BaltorkI., and Ramzanian-LehmaliF., J. Chem. Res. (S), 2001, 185.
26.
ScheerenJ.W., OomsP. H. J, and NivardR. J. F., Synthesis, 1973, 149
27.
(a) FieserL.F., and FieserM., “Reagents for Organic Synthesis”, Wiley, New York, 1967, Vol. 1, pp. 333; (b) B. S. Pedersen, S. Scheibye, N. H. Nilsson and S.-O. Lawesson, Bull. Soc. Chim. Belg, 1978, 87, 223; (c) B. S. Pedersen, S. Scheibye, K. Clausen and S.-O. Lawesson, Bull. Soc. Chim. Belg., 1978, 87, 293.
28.
(a) Vogel's, “Textbook of Practical Organic Chemistry”, Fifth Ed., John Wiley & Sons, Inc., New York, 1989; (b) Dictionary of Organic Compounds, Sixth Ed., Chapman & Hall, 1996; (c) Beilsteins Handbuch der Organischen Chemie Vierte Auflage; (d) Aldrich Catalogue Handbook of Fine Chemicals, 1999-2000.