Bahador KARAMI, Morteza MONTAZEROZOHORI, Majid MOGHADAM, Mohammad Hosein HABIBI, Khodabakhsh NIKNAM

Selective Oxidation of Thiols to Disulfides Catalyzed by Iron(III) -- Tetra Phenyl Porphyrin Using Urea-Hydrogen Peroxide as Oxidizing Reagent

Oxidation of thiols to disulfides catalyzed by iron(III) -- tetra phenyl prophyrin Fe (TPP)Cl was investigated using urea-hydrogen peroxide adduct (UHP) as an oxidant in methanol as a solvent.

Anahtar Kelimeler:

Thiols, Fe (TPP) Cl, Urea hydrogen peroxide, disulfides

Selective Oxidation of Thiols to Disulfides Catalyzed by Iron(III) -- Tetra Phenyl Porphyrin Using Urea-Hydrogen Peroxide as Oxidizing Reagent

Oxidation of thiols to disulfides catalyzed by iron(III) -- tetra phenyl prophyrin Fe (TPP)Cl was investigated using urea-hydrogen peroxide adduct (UHP) as an oxidant in methanol as a solvent.

Keywords:

Thiols, Fe (TPP) Cl, Urea hydrogen peroxide, disulfides,

PDF

___

D.C. Jocelyn, Biochemistry of the Thiol Group, Academic Press: New York, 1992.
G. Capozzi and G. Modena, The Chemistry of Thiol Group, Part 2; S. Patai, Ed., pp. 785, Wiley: New York, 1974.
I. Pe’er, C.E. Felder, O. Man, I. Silman and J.L. Sussman, Proteins 54, 20-40 (2004).
J.C. Bardwell, Mol. Microbiol. 14, 199-205 (1994).
N. Kharasch and A.S. Arora, Phosphorus and Sulfur 2, 1 (1976).
E. Kuhle, The Chemistry of the Sulfenic Acids, Georg Thieme Verlag Stuttgart, 1973.
I.B. Douglass and R.V. Norton, J. Org. Chem. 33, 2104 (1968).
I.B. Douglass, J. Org. Chem. 39, 563 (1974).
M.M. Khodaei, I. Mohammadpoor-Baltork and K. Nikoofar, Bull. Korean Chem. Soc. 24, 885 (2003).
A. McKillop, D. Koyuncu, A. Krief, W. Dumont, P. Renier and M. Trabelsi, Tetrahedron Lett. 31, 5007 (1990).
G.B. Jensen, G. Smith, D.S. Sagatys, P.C. Healyb and J.M. White, Acta Cryst. E 60, 2438 (2004).
A. Khazaei, M.A. Zolfigol and A.Rostami, Synthesis 2959 (2004).
L.W. Christensen and D.J. Heacock, Synthesis 50 (1978).
J.Drabowicz and M. Mikolajczyk, Synthesis 32 (1980).
H. Firouzabadi and I. Mohammadpoor-Baltork, Bull. Chem. Soc. Jpn. 65, 1485 (1992).
N. Iranpoor, H. Firouzabadi and M.A. Zolfigol, Synth. Commun. 28, 367 (1998).
N. Iranpoor and B. Zeynizadeh, Synthesis 49 (1999).
A. McKillop and D. Koyuncu, Tetrahedron Lett. 31, 5007 (1990).
X. Wu, R.D. Rieke and L. Zhu, Synth. Commun. 26, 191 (1996).
H.M. Meshram and R. Kache, Synth. Commun. 27, 2403 (1997).
M. Hirano, S. Yakabe, K.-I. Ando and T. Morimoto, J. Chem. Res. (S), 816 (1998).
M. Hirano, S. Yakabe, H. Monobe and T. Morimoto, J. Chem. Res. (S), 472 (1998).
M. Sridhar, S.K.Vadivel and U.T. Bhalerao, Synth.Commun. 28, 1499 (1998).
T.V. Rao, B. Sain, P.S.Murthy, T.S.R.P. Rao, A.K. Jain and G.C. Joshi, J. Chem. Res. (S), 300 (1997).
M.C. Noureldine, J. Hendry and D.G. Lee, Synthesis 1587 (1998).
V. Kesavan, D. Bonnet-Delpon and J.-P. Begue, Synthesis 223 (2000).
B. Movassagh, M.M. Lakouraj and K. Ghodrati, Synth. Commun. 29, 3597 (1999).
A.R. Hajipour and S.E. Mallakpour, J. Chem. Res. (S), 32 (2000).
S. Raghavan, A. Rajender, S.C. Joseph and M. A. Rasheed, Synth. Commun. 31, 1477 (2001).
P. Salehi, A. Farrokhiand and M. Gholizadeh, Synth. Commun. 31, 2777 (2001).
J.-X. Wang, L. Gao and D. Huang, Synth. Commun. 32, 963 (2002).
Y.- H. Sun and K.-Y. Ko, Bull. Korean Chem. Soc. 21, 669 (2000).
F.-E. Chen, Y.-W. Lu, Y.-P. He, Y.-F. Luo and M.-G. Yan, Synth. Commun. 32, 3487 (2002).
M.J. Coon and R.E. White, Dioxygen Binding and Activation by Metal Centers, T.G. Spiro, Ed., pp.73, Wiley: New York, 1980.
R.E. White and M. Coon, J. Annu. Rev. Biochem. 49, 315 (1980).
J.R. Lindsay Smith and D.N. Mortimer, J. Chem. Soc., Perkin Trans. 2, 1743 (1986).
A.J. Appelton, S. Evans and J.R. Lindsay Smith, J. Chem. Soc., Perkin Trans. 2, 281 (1996).
P. Hoffman, A. Robert and B. Meunier, Bull. Soc. Chim. Fr. 129, 85 (1992).
A. Maldotti, C. Bartocci, G. Varani, A. Molinari, P. Battioni and D. Mansuy, Inorg. Chem. 35, 1126 (1996).
D. Dolphin, T.G. Traylor and L.Y. Xie, Acc. Chem. Res. 30, 251 (1997).
K.A. Jorgenson, J. Chem. Soc., Chem. Commun. 1405 (1987).
S. Tollari, D. Vergani, S. Banfi and F. Porta, J. Chem. Soc., Chem. Commun. 442 (1993).
J.T. Groves and T.E. Nemo, J. Am. Chem. Soc. 105, 5786 (1983).
O. Bortolini and B. Meunier, J. Chem. Soc. Perkin Trans. 2, 1967 (1984).
B. Meunier, E. Cuilmel, M.E. De Carvallho and R. Poiblane, J. Am. Chem. Soc. 106, 6668 (1984).
D. Mohajer and S. Tangestaninejad, J. Chem. Soc., Chem. Commun. 240 (1993).
D. Mohajer and S. Tangestaninejad, Tetrahedron Lett. 35, 945 (1994).
D. Wohler and J. Gitzel, Makromol. Chem., Rapid Commun. 9, 229 (1988).
D.R. Leonard and J.R. Lindsay Smith, J. Chem. Soc. Perkin Trans. 2, 1917 (1990);
D.R. Leonard and J.R. Lindsay Smith, J. Chem. Soc. Perkin Trans. 2, 25 (1991).
L. Astodillo, A. Galindo, A.G. Gonzalez and H. Mansilla, Heterocycles 36, 1075 (1993).
T. Uchida and T. Katsuki, Tetrahedron Lett. 42, 6911 (2001).
R. Balicki, Synth. Commun. 29, 2235 (1999).
H. Heaney and A.J. Newbold, Tetrahedron Lett. 42, 6607 (2001).
P. Pietikainen, J. Mol. Cat. A: Chem. 165, 73 (2001).
R.I. Kureshy, N.H. Khan, S.H.R. Abdi, S.T. Patel and R.V. Jasra, Tetrahedron: Asymmetry 12, 433 (2001).
J.A. Damavandi, B. Karami and M.A. Zolfigol, Synlett 933 (2002).
P. Pietikainen, J. Mol. Catal. A: Chem. 165, 73-79 (2001), references therein.
N.A. Noureldin, D. Zhao and D.G. Lee, J. Org. Chem. 62, 8767 (1997).
S. Bunnai and K.Tsutomu, Tetrahedron Lett. 42, 3873 (2001).
U. Tatsuya and K. Tsutomu, Tetrahedron Lett. 42, 6911 (2001).
A. Chellamani, N.M.I. Alhaji, S. Rajagopal, R. Sevvel and C. Srinivasan, Tetrahedron 51, 12677 (1995);
A. Chellamani, N.M.I. Alhaji and S. Rajagopal, J. Chem. Soc., Perkin Trans. 2, 299 (1997).
K. Katsuki, J. Mol. Catal. A: Chem. 113, 87 (1996).
A.D. Adler, F.R. Longor, J.D. Finarelli, J. Goldmacher, J. Assour and L. Korsakoff, J. Org. Chem. 32, 476 (1967).
T. Aida, T. Akasaka, N. Furukawa and S. Oae, Bull. Chem. Soc. Jpn. 49, 1441 (1976).
W.E. Fristad and J.R. Peterson, Synth. Commun. 15, 1 (1985).