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2005 | 3 | 1 | 63-71
Tytuł artykułu

Oxidation of α-methylstyrene on an MCM-22 encapsulated (R, R)-(−)-N, N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) catalyst

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
(R, R)-(−)-N, N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) was encapsulated into MCM-22 using the zeolite synthesis method. The encapsulated catalyst proved to be active in the oxidation of α-methylstyrene with NaOCl with higher specific activity than the homogeneous catalyst. At the same time, this encapsulated catalyst was completely inactive in the hydrolytic kinetic resolution of racemic styrene oxide. This observation is in a good correlation with the assumption of the cooperative bimetallic mechanism proposed by Annis and Jacobsen.
Wydawca

Czasopismo
Rocznik
Tom
3
Numer
1
Strony
63-71
Opis fizyczny
Daty
wydano
2005-03-01
online
2005-03-01
Bibliografia
  • [1] D.E. De Vos, I.F.J. Vankelecom and P.A. Jacobs: Chiral Catalyst Immobilization and Recycling, Wiley-VCH, Weinheim, 2000.
  • [2] D.E. De Vos, M. Dams, B.F. Sels and P.A. Jacobs: “Ordered Mesoporous and Microporous Molecular Sieves Functionalized with Transition Metal Complexes as Catalysts for Selective Organic Transformations”, Chem. Rev., Vol. 102, (2002), pp. 3615–3640. http://dx.doi.org/10.1021/cr010368u[Crossref]
  • [3] C. Bianchini and P. Barbaro: “Recent aspects of asymmetric catalysis by immobilized chiral metal catalysts”, Topics Catal., Vol. 19, (2002), pp. 17–32. http://dx.doi.org/10.1023/A:1013825114636[Crossref]
  • [4] M.J. Sabater, A. Corma, A. Domenech, V. Fornes and H. Garcia: “Chiral salen maganese complex encapsulated within zeolite Y: a heterogeneous enantioselective catalyst for the epoxidation of alkenes”, J. Chem. Soc., Chem. Commun., (1997), pp. 1285–1286. [Crossref]
  • [5] S.B. Ogunwumi and T. Bein: “Intrazeolite assembly of a chiral manganese salen expoxidation catalysts”, J. Chem. Soc., Chem. Commun., (1997), pp. 901–902. [Crossref]
  • [6] C. Reyes, Y. Gao, Á. Zsigmond, P. Goel, N. Mahata, S. Tanielyan and R.L. Augustine: “Solvent Effects in the Use of Anchored Homogeneous Catalyst for Hydrogenation Reactions”, Chemistry Industry (Dekker), Vol. 89, (2002), pp. 627–632.
  • [7] R.L. Augustine, S.K. Tanielyan, N. Mahata, Y Gao, Á. Zsigmond and H. Yang: “Anchored homogeneous catalysts: The role of the heteropoly acid anchoring agent”, Appl. Catal. A-General, Vol. 256, (2003), pp. 69–76. http://dx.doi.org/10.1016/S0926-860X(03)00389-2[Crossref]
  • [8] Á. Zsigmond, K. Bogár and F. Notheisz: “Comparative study of “Ship-in-a-bottle” and Anchored Rh Complexes”, J. Catal., Vol. 213, (2003), pp. 103–108. http://dx.doi.org/10.1016/S0021-9517(02)00023-4[Crossref][WoS]
  • [9] M. E. Leonowicz, J.A. Lawton and M.K. Rubin: “MCM-22-a molecular sieve with two independent multidimensional channel systems”, Science, Vol. 264, (1994), pp. 1910–1913. http://dx.doi.org/10.1126/science.264.5167.1910[Crossref]
  • [10] G. Gbery, Á. Zsigmond and D.J. Balkus, Jr.: “Enantioselective epoxidations catalyzed by zeolite MCM-22 encapsulated Jacobsen’s catalyst”, Catal. Lett., Vol. 74, (2001), pp. 77–80. http://dx.doi.org/10.1023/A:1016682606382[Crossref]
  • [11] Á. Zsigmond, F. Notheisz, Z. Fráter and J.E. Bäckvall: “Selective oxidation of alcohols on zeolite encapsulated cobalt salophen catalysts”, Studies in Surface Science and Catalysis, Vol. 108, (1997), pp. 453–459.
  • [12] Á. Zsigmond, F. Notheisz, G. Csjernyik and J.E. Bäckvall: “Ruthenium-catalyzed aerobic oxidation of alcohols on zeolite-encapsulated cobalt salophen catalyst”, Top. Catal., Vol. 19, (2002), pp. 119–124. http://dx.doi.org/10.1023/A:1013893502340[Crossref]
  • [13] R.G Konsler, J. Kaarl and E.N. Jacobsen: “Cooperative asymmetric catalysis with dimeric salen complexes”, J. Am. Chem. Soc., Vol. 120, (1998), pp. 10780–10781. http://dx.doi.org/10.1021/ja982683c[Crossref]
  • [14] M. Tokunaga, J.F. Larrow, F. Kakuchi and E.N. Jacobsen: “Asymmetric catalysis with water: Efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis”, Science, Vol. 277, (1997), pp. 936–938. http://dx.doi.org/10.1126/science.277.5328.936[Crossref]
  • [15] K.B. Hansen, J.L. Leighton and E.N. Jacobsen: “On the mechanism of asymmetric nucleophilic ring-opening of epoxides catalyzed by (salen)Cr-III complexes”, J. Am. Chem. Soc., Vol. 118, (1996), pp. 10924–10925. http://dx.doi.org/10.1021/ja962600x[Crossref]
  • [16] D.A. Annis and E.N. Jacobsen: “Polymer-supported chiral Co(salen) complexes: Synthetic applications and mechanistic investigations in the hydrolytic kinetic resolution of terminal epoxides”, J. Am. Chem. Soc., Vol. 121, (1999), pp. 4147–4154. http://dx.doi.org/10.1021/ja984410n[Crossref]
  • [17] I. Guray, J. Warzywoda, N. Bac and A. Sacco, Jr.: “Synthesis of zeolite MCM-22 under rotating and static conditions”, Microporous Mesoporous Mater., Vol. 31, (1999), pp. 241–251. http://dx.doi.org/10.1016/S1387-1811(99)00075-X[Crossref]
  • [18] F. Notheisz, Á. Zsigmond, Zs. Szegletes and J.E. Bäckvall: “Aerobic oxidations on metal macrocycles encapsulated in zeolites”, Studies in Surface Science and Catalysis, Vol. 94, (1995), pp. 728–735. http://dx.doi.org/10.1016/S0167-2991(06)81290-5[Crossref]
  • [19] Á. Zsigmond, F. Notheisz and J.E. Bäckvall: “Rate enhancement of oxidation reactions by the encapsulation of metal phthalocyanine complex”, Catal. Lett., Vol. 65, (2000), pp. 135–139. http://dx.doi.org/10.1023/A:1019005018899[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_BF02476238
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