1,4-bis(triphenyl phosphonium)butane peroxodisulfate: conversion of alkyl benzenes to carbonyl compounds

Document Type: Original Paper

Authors

Islamic Azad University , Science and Research Branch , Ahvaz, Iran.

Abstract

1,4-bis(triphenyl phosphonium)butane peroxodisulfate(BTPPBPDS) were synthesized by treating 1,4-bis(triphenyl phosphonium)butane dibromide and potassium peroxydisulfate in aqueous solution.This was used mild and efficient reagent for oxidation of alkyl benzenes to their corresponding carbonyl compounds in very good to high yields.

Keywords


1. (a) D. A. House, Chem. Re 62 ,.ט , 185 (1962); (b) E. J. Behrman and J. E. McIssac,
Annual Reports on Mechanisms of Reactions of Sulfur Compounds, vol. 2, Intra-Science
Research Foundation, Santa Monica, Calif., 1968, p 235.
2. W. K. Wilmarth and A. Haim, “Peroxide Reaction Mechanisms,” J. O. Edwards, Ed.,
John Wiley & Sons, Inc., New York, N.Y., 1962, p 175 ff.
3. (a) R. G. R. Bacon, W. J. W. Hanna, and D. Stewart, J. Chem. Soc., C, 1384, 1388
(1966); (b) ibid., 1332, 1339 (1960); (c) ibid., 2275 (1954); Proc. Chem. Soc., 113
(1962); (d) G. D. Menghani and G. V. Bakore, Bull. Chem. Soc. Japan, 41, 2547 (1968).
4. I. Mohammadpoor-Baltork, A. R. Hajipour, R. Haddadi, J. Chem. Res, 102 (1992).

5. M. M. Hashemi, Y. Ahmadi Beni, J. Chem. Res, 434 (1999).
6. I. Mohammadpoor-Baltork, A. R. Hajipour, H. Mohammadi, Bull. Chem. Soc. Japan, 71, 1649 (1998).
7. R. Varma, H. M. Meshran, Tetrahedron Lett. 5427 (1997).
8. B. Didier, C. Philipe, Tetrahedron Lett. 43, 7725 (1996).
9. F. Chen, J. Wan, C. Guam, J. Yang, H. Zhang, Synth. Commun. 253 (1996).
10. P. Dave, H. S. Byum, R. Engel, Synth. Commun. 16, 1343 (1986).
11. The problem is complicated by the ready induced decomposition of peroxydisulfate and the chain character of many of these reactions.