PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Czasopismo
2008 | 6 | 2 | 145-153
Tytuł artykułu

Iron porphyrins-catalysed oxidation of α-alkyl substituted mono and dimethoxylated benzyl alcohols

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The mechanisms of oxidation of a series of a-alkyl substituted mono and dimethoxylated benzyl alcohols catalysed by mesotetrakis(4-N-methylpyridynium)porphyrin iron (III) chloride (FeTMPyPCl) and meso-tetrakis(4-sulfonatophenyl)porphyrin iron (III) chloride (FeTSPPCl) in aqueous solution with KHSO5 as oxygen atom donor and by meso-tetrakis(pentafluorophenyl)-porphyrin iron (III) chloride (FeTPFPPCl) in dichloromethane employing iodosylbenzene as oxidant have been investigated. In the highly polar aqueous medium an electron transfer mechanism is operating. With FeTMPyPCl, which is a much more efficient catalyst than FeTSPPCl due to the presence of stronger electron withdrawing substituents, formation of side-chain oxidation products accompanies generation of nuclear oxidation products. In the low polar solvent dichloromethane, two competing mechanism have been suggested: hydrogen atom transfer and formation of a complex between the active species iron-oxo porphyrin radical cation and the substrate. [...]
Słowa kluczowe
Wydawca

Czasopismo
Rocznik
Tom
6
Numer
2
Strony
145-153
Opis fizyczny
Daty
wydano
2008-06-01
online
2008-04-17
Twórcy
  • Dipartimento di Chimica, Sapienza Università di Roma and Istituto CNR di Metodologie Chimiche (IMC-CNR), Sezione Meccanismi di Reazione, P.le Aldo Moro 5, 00185, Rome, Italy
  • Dipartimento di Chimica, Sapienza Università di Roma and Istituto CNR di Metodologie Chimiche (IMC-CNR), Sezione Meccanismi di Reazione, P.le Aldo Moro 5, 00185, Rome, Italy
  • Dipartimento di Chimica, Sapienza Università di Roma and Istituto CNR di Metodologie Chimiche (IMC-CNR), Sezione Meccanismi di Reazione, P.le Aldo Moro 5, 00185, Rome, Italy, lanzalunga@uniroma1.it
Bibliografia
  • [1] B. Meunier, Chem. Rev., 92, 1411 (1992) http://dx.doi.org/10.1021/cr00014a008[Crossref]
  • [2] R.A. Sheldon (Ed.): Metalloporphyrins in Catalytic Oxidations (Marcel Dekker, New York, 1994)
  • [3] D.R. Leonard, J.R. Lindsay Smith, J. Chem. Soc. Perk. Trans. II, 1917 (1990) http://dx.doi.org/10.1039/p29900001917[Crossref]
  • [4] E.B. Fleisher, J.M. Palmer, T.S. Srivastava, A. Chatterjce, J. Am. Chem. Soc., 93, 3162 (1971) http://dx.doi.org/10.1021/ja00742a012[Crossref]
  • [5] B. Meunier, A. Robert, G. Pratviel, J. Bernadou: “Metalloporphyrins in Catalytic Oxidation and Oxidative DNA Cleavage”, K. M. Kadish, K. M. Smith, R. Guilard (Eds.), in The Porphyrin Handbook, (Academic Press, New York, 2000)
  • [6] J. T. Groves, R. C. Haushalter, M. Nakamura, T. E. Nemo, B. J. Evans, J. Am. Chem. Soc., 103, 2884 (1981) http://dx.doi.org/10.1021/ja00400a075[Crossref]
  • [7] J. R. Lindsay Smith, D. N. Mortimer, J. Chem. Soc., Chem. Commun., 64 (1985) [Crossref]
  • [8] J. R. Lindsay Smith, D. N. Mortimer, J. Chem. Soc. Perk. Trans. II, 1743 (1986) http://dx.doi.org/10.1039/p29860001743[Crossref]
  • [9] J. Bernadou, B. Meunier, Adv. Synth. Catal., 346, 171 (2004) http://dx.doi.org/10.1002/adsc.200303191[Crossref]
  • [10] R. Zhang, R. Esala, P. Chandrasena, E. Martinez II, J.H. Horner, M. Newcomb, Org. Lett., 7, 1193 (2005) http://dx.doi.org/10.1021/ol050296j[Crossref]
  • [11] Z. Pan, M. Newcomb, Inorg. Chem., 46, 6767 (2007) http://dx.doi.org/10.1021/ic700395j[Crossref]
  • [12] H.-R. Biørsvik, F. Minisci, Org. Proc. Res. & Dev., 3, 330 (1999) http://dx.doi.org/10.1021/op9900028[Crossref]
  • [13] J.C. Roberts (Ed.): The Chemistry of Paper, The Royal Society of Chemistry, Cambridge, UK, 1996
  • [14] D. Dolphin, T. Nakano, T.E. Maione, T.K. Kirk, R. Farrel: “Lignin Enzymic and Microbial Degradation”, INRA (Ed.), Paris, 157–162, 1987
  • [15] G. Labat, B. Meunier, J. Org. Chem., 54, 5008 (1989) http://dx.doi.org/10.1021/jo00282a011[Crossref]
  • [16] F. Cui, D. Dolphin, Can. J. Chem, 70, 2314 (1992) http://dx.doi.org/10.1139/v92-292[Crossref]
  • [17] G. Labat, B. Meunier, New J. Chem., 13, 801 (1989)
  • [18] R. Dicosimo, H.-C. Szabo, ACS Symposium Series, Biocatal. Biomimetics, 392, 123 (1989)
  • [19] C. Crestini, R. Saladino, P. Tagliatesta, T. Boschi, Bioorg. Med. Chem., 7, 1897 (1999) http://dx.doi.org/10.1016/S0968-0896(99)00105-4[Crossref]
  • [20] K. Wiezetzerbin, B. Meunier, J. Bernadou, Chem Commun., 2321 (1997) [Crossref]
  • [21] I. Artaud, K. Ben-Aziza, D. Mansuy, J. Org. Chem, 58, 3373 (1993) http://dx.doi.org/10.1021/jo00064a026[Crossref]
  • [22] C.K. Chang, F. Ebina, J. Chem. Soc., Chem. Commun., 778 (1981) [Crossref]
  • [23] J. F. Bartoli, O. Brigaud, P. Battioni, D. Mansuy, J. Chem. Soc., Chem. Commun., 440 (1991) [Crossref]
  • [24] E. Baciocchi, O. Lanzalunga, A. Lapi, L. Manduchi, J. Am. Chem. Soc., 120, 5783 (1995) http://dx.doi.org/10.1021/ja980187i[Crossref]
  • [25] W. Nam, M.H. Lim, H.J. Lee, C. Kim, J. Am. Chem. Soc., 122, 6641 (2000) http://dx.doi.org/10.1021/ja000289k[Crossref]
  • [26] W. Nam, S. W. Jin, M.H. Lim, J.Y. Ryu, C. Kim, Inorg. Chem., 41, 3647 (2002) http://dx.doi.org/10.1021/ic011145p[Crossref]
  • [27] L. Eberson, J. Am. Chem. Soc., 105, 3192 (1983) http://dx.doi.org/10.1021/ja00348a039[Crossref]
  • [28] E. Baciocchi, M. Crescenzi, E. Fasella, M. Mattioli, J. Org. Chem., 57, 4684 (1992) http://dx.doi.org/10.1021/jo00043a028[Crossref]
  • [29] H. Saltzman, J. G. Sharefkin, Org. Synthesis, 43, 60 (1963).
  • [30] E. Baciocchi, S. Belvedere, M. Bietti, O. Lanzalunga, Eur. J. Org. Chem. 2, 299 (1998) http://dx.doi.org/10.1002/(SICI)1099-0690(199802)1998:2<299::AID-EJOC299>3.0.CO;2-B
  • [31] Vogel’s: Textbook of Practical Organic Chemistry, 5th edition (Harlow, Longman, UK, (1989)
  • [32] H.W.H. Schmidt, S.H. Haemmerli, H.S. Schoemaker, M.S.A. Leisola, Biochemisty, 28, 1776 (1989) http://dx.doi.org/10.1021/bi00430a053[Crossref]
  • [33] The results of the oxidation of substrates 1–4 with the FeTFPPCl/PhIO system are reported in the literature. See E. Baciocchi, S. Belvedere, M. Bietti, Tetrahedron Lett., 39, 4711 (1998) [Crossref]
  • [34] E. Baciocchi, C. Fabbri, O. Lanzalunga, J. Org. Chem., 68, 9061 (2003) http://dx.doi.org/10.1021/jo035052w[Crossref]
  • [35] It is likely that 4-methoxybenzaldehyde is also formed as minor product in the oxidation of 3 by the FeTMPyPCl/KHSO5 system, however the substrate conversion was too low to reveal traces of this product. No products have been observed in the reaction of 4 with the FeTPPSCl/KHSO5 system
  • [36] The oxidation potential of 4-methoxybenzylalcohol (1.8 V vs NHE) [37] is ca 0.54 V higher than that of 3,4-dimethoxybenzyl alcohol (1.36 V vs NHE) [38]
  • [37] G. Cantarella, C. Galli, P. Gentili, New J. Chem., 28, 366 (2004) http://dx.doi.org/10.1039/b311907f[Crossref]
  • [38] M. Bietti, E. Baciocchi, S. Steenken, J. Phys. Chem. A, 102, 7337 (1998) http://dx.doi.org/10.1021/jp9812482[Crossref]
  • [39] H. Fujii, J. Am. Chem. Soc., 115, 4641 (1993) http://dx.doi.org/10.1021/ja00064a027[Crossref]
  • [40] W. Nam et al., J. Am. Chem. Soc., 122, 8677 (2000) http://dx.doi.org/10.1021/ja994403e[Crossref]
  • [41] It has to be noted that in this study a different solvent (butyronitrile) has been used. N.Y. Oh et al., Angew. Chem. Int. Ed., 44, 4235 (2005) http://dx.doi.org/10.1002/anie.200500623[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-008-0005-8
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.