p-Toluenesulfonic acid a useful and selective reagent for the oxidation of benzoins to benziles under solvent-free condition
الموضوعات : Journal of the Iranian Chemical Research
Nader Noroozi Pesyan
1
(Department of Chemistry, Faculty of Science, Urmia University, Urmia, Iran)
Abdul Hossein Abdul Hossein Dabbagh
2
(College of Chemistry, Isfahan University of Technology, Isfahan, Iran)
الکلمات المفتاحية: Solvent-free, Benzoins, Benziles, α-Diketones, p-Toluenesulfonic acid (PTSA),
ملخص المقالة :
Oxidation of some benzoins to benziles is reported by using p-toluenesulfonic acid as aselective oxidation catalyst under solvent-free condition in high yield. The adjacent carbonylgroup is necessary for the oxidation of hydroxyl group in these compounds. The reaction iscarried out in a sand-bath at 100 °C with minimum by-products.
[1] R.L. Hudkins, D.L. DeHaven-Hudkins, Bioorg. Med. Chem. Lett. 4 (1994) 2185.
[2] C.G. Bonde, N.J. Gaikwad, Bioorg. Med. Chem. 12 (2004) 2151.
[3] B. Jiang, X.-H. Gu, Bioorg. Med. Chem. 8 (2000) 363.
[4] B.S. Jursic, D.M. Neumann, K.L. Martin, E.D. Stevens, Org. Lett. 4 (2002) 811.
[5] J. March, Advanced Organic Chemistry Reaction Mechanisms and Structure, 3th Edition, John Wiley,
New York, 1985, p. 1077.
[6] N. Iranpoor, H. Firouzabadi, M.A. Zolfigol, Bull. Chem. Soc. Jpn. 71 (1998) 905.
[7] H.A. Cannon, B.G. Sheldon, K.E. Harding, L.E. Letterman, D.C. Fulton, W.G. Nigh, J. Org. Chem.
38 (1973) 2020.
[8] J. Yamamoto, S. Ito, T. Tsuboi, T. Tsuboi, K. Tsukihara, Bull. Chem. Soc. Jpn. 58 (1985) 470.
[9] A. Mckillop, B.P. Swann, M.E. Ford, E.C Taylor, J. Am. Chem., Soc. 95 (1973) 3641.
[10] B. Tamami, N. Goudarzian, Polymer Bull. 23 (1990) 295.
[11] K. Alok, M. Apra De, N. Karchaudhuri, J. Chem. Res. (S) (1999) 246.
[12] G.S. Hammond, C.H.S. Wu, J. Am. Chem. Soc. 95 (1973) 8215.
[13] A.R. Hajipour, S.E. Mallakpour, I.M. Baltork, S Khoee, Chem. Lett. (2000) 120.
[14] A.R. Hajipour, I.M. Baltork, Phos. Sulfor and Silicon 164 (2000) 145.
[15] I.M. Baltork, A.R. Hajipour, A. Ghahramankhani, Indian J. Chem. Sec B 39 (2000) 863.
[16] N. Noroozi-Pesyan, A.H. Dabbagh, Molecules 10 (2005) 1364.
[17] J.D. Albright, J. Org. Chem. 39 (1974) 1977.
[18] S.K. Kar, A. Kar, J. Org. Chem. 42 (1977) 390.
[19] (a) F. Toda, H. Takumi, M. Akehi, J. Chem. Soc. Chem. Commun. (1990) 1270, (b) F. Toda, K.
Okuda, J. Chem. Soc. Chem. Commun. (1991) 1212.
[20] W.S. Ide, J.S. Buck, Organic React. 4 (1948) 269.
[21] A. Giraud, O. Provot, J.-F. Peyrat, M. Alami, J.-D. Brion, Tetrahedrton 62 (2006) 7667.
[22] D.R. Berger, R.K. Summerbell, J. Org. Chem. 24 (1959) 1881.
[23] D.H.R. Barton, I.A. Blair, P.D. Magnus, R. K. Norris, J. Chem. Soc., Perkin Trans. 1 (1973) 1037.
