Activation of H2O2 by methyltrioxorhenium(VII) inside β-cyclodextrin

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 70, Issue 3-4, 2011, Pages 471-480

  Al Rawashdeh, N A F ^a,b   Al Ajlouni, A M ^b   Bukallah, S B ^a   Bataineh, N ^b,c  

^a UNITED ARAB EMIRATES UNIVERSITY   (United Arab Emirates)

^b JORDAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Jordan)

^c UNIVERSITY OF VERMONT   (United States)

Author keywords

Activation of hydrogen peroxide; Catalysis; Inclusion complex; Oxidation of indigo dye; Rhenium complexes

Indexed keywords

EID: 80051789195     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-010-9876-3     Document Type: Conference Paper

References (34)

1. Laszlo, P.; Levart, M.; Bouhlel, E.; Montaufier, M.; Singh, G.P.; Oyama, S.T.; Hightower, J.W. (eds.): Catalytic Selective Oxidation, Chapter 4. American Chemical Society, Washington, DC (1993)
2. AM Al-Ajlouni JH Espenson 1996 Kinetics and mechanism of the epoxidation of alkyl-substituted alkenes by hydrogen peorxide, catalyzed by methylrhenium trioxid J. Org. Chem. 61 3969 3976 10.1021/jo951774e 1:CAS:528: DyaK28XjtFymtLk%3D (Pubitemid 126552413)
3. Herrmann, W.A.: Olefins from Aldehydes in Applied Homogeneous Catalysis with Organometallic Compounds, 2nd edn, vol. 3, pp. 1078-1086. Wiley VCH, Weinheim, Germany (2002)
4. 2 systems for the oxidation of lignin and lignin model compounds Bioorg. Med. Chem. 14 5292 5302 10.1016/j.bmc.2006.03.046 1:CAS:528:DC%2BD28XlvFyru78%3D (Pubitemid 43903253)
5. 2 and polymer-supported methylrheniumtrioxide systems Tetrahedron 59 7403 7408 10.1016/S0040-4020(03) 01145-1 1:CAS:528:DC%2BD3sXmvFSjsrk%3D (Pubitemid 37087996)
6. Z Zhu JH Espenson 1995 Oxidation of alkynes by hydrogen peroxide catalyzed by methylrhenium trioxide J. Org. Chem. 60 7728 7732 10.1021/jo00129a010 1:CAS:528:DyaK2MXpt1antbo%3D
7. W Adam WA Herrmann CR Saha-Moller M Shimizu 1995 Oxidation of methoxybenzenes to p-benzoquinones catalyzed by methyltrioxorhenium(VII) J. Mol. Catal. A Chem. 97 15 20 10.1016/1381-1169(94)00070-0 1:CAS:528: DyaK2MXksFCju7w%3D
8. 2 catalytic system Tetrahedron Lett. 42 5401 5404 10.1016/S0040-4039(01)01005-X 1:CAS:528:DC%2BD3MXltFymsrY%3D (Pubitemid 32709793)
9. 2 in air Tetrahedron Lett. 37 6487 6490 10.1016/0040-4039(96)01418-9 1:CAS:528:DyaK28Xls12ktLo%3D (Pubitemid 26278269)
10. W Adam WA Herrmann J Lin CR Saha-Moller 1994 Catalytic oxidation of phenols to p-quinones with the hydrogen peroxide and methyltrioxorhenium(VII) system J. Org. Chem. 59 8281 8283 10.1021/jo00105a058 1:CAS:528: DyaK2MXitlWntrg%3D
11. G Soldaini F Cardona A Goti 2003 Methyltrioxorhenium catalyzed domino epoxidation-nucleophilic ring opening of glycals Tetrahedron Lett. 44 5589 5592 10.1016/S0040-4039(03)01386-8 1:CAS:528:DC%2BD3sXkvFGisbs%3D (Pubitemid 36782585)
12. 3 Steroids 71 565 577 10.1016/j.steroids.2006.02.003 1:CAS:528:DC%2BD28XltFCktLs%3D (Pubitemid 43766940)
13. Z Zhang J Wang 2008 Recent studies on the reactions of α-diazocarbonyl compounds Tetrahedron 64 6577 6605 10.1016/j.tet.2008.04. 074 1:CAS:528:DC%2BD1cXnt1Kqt78%3D
14. 3 bond J. Am. Chem. Soc. 129 15794 15804 10.1021/ja0714742 1:CAS:528:DC%2BD2sXhtlynu7%2FJ
15. WA Herrmann RW Fischer DW Marz 1991 Methyltrioxorhenium as catalyst for olefin oxidation Angew. Chem. Int. Ed. Engl. 30 1638 1641 10.1002/anie.199116381
16. Z Petrovski SS Braga AM Santos SS Rodrigues IS Goncalves M Pillinger FE Kuhn CC Romao 2005 Synthesis and characterization of the inclusion compound of a ferrocenyldiimine dioxomolybdenum complex with heptakis-2,3,6-tri-O-methyl- β-cyclodextrin Inorg. Chim. Acta 358 981 988 10.1016/j.ica.2004.11.032 1:CAS:528:DC%2BD2MXhsVOgsro%3D (Pubitemid 40260973)
17. SS Braga S Gago JD Seixas AA Valente M Pillinger TM Santos IS Goncalves CC Romao 2006 β-Cyclodextrin and permethylated β-cyclodextrin inclusion compounds of a cylopentadienyl molybdenum tricarbonyl complex and their use as cyclooctene epoxidation catalyst precursors Inorg. Chim. Acta 359 4757 4764 10.1016/j.ica.2006.03.017 1:CAS:528:DC%2BD28Xht1WltbnK
18. L Caron H Bricout S Tilloy A Ponchel D Landy S Fourmentin E Monflier 2004 Molecular recognition between a water-soluble organometallic complex and a β-cyclodextrin: first example of second-sphere coordination adducts possessing a catalytic activity Adv. Synth. Catal. 346 1449 1456 10.1002/adsc.200404104 1:CAS:528:DC%2BD2cXpvVygsLg%3D (Pubitemid 39539670)
19. Fenyvesi, E.; Szente, L.; Russel, N.R.; McNamara, M.: In: Szejtli, J.; Osa, T. (eds.) Comprehensive Supramolecular Chemistry, vol. 3, p. 305. Pergamon Press, Oxford, UK (1996)
20. G Soldaini F Cardona A Goti 2007 Catalytic oxidation of imines based on methyltrioxorhenium/urea hyrogen peroxide: a mild and easy chemo- and regioselective entry to nitrones Org. Lett. 9 473 476 10.1021/ol062862w 1:CAS:528:DC%2BD2sXovVOj
21. G Yin DH Busch 2009 Mechanistic details of facilitate applications of an exceptional catalyst, methyltrioxorhenium: encouraging results from oxygen-18 isotopic probes Catal. Lett. 130 52 55 10.1007/s10562-009-9855-8 1:CAS:528:DC%2BD1MXisFOktrg%3D
22. MM Abu-Omar PJ Hansen JH Espenson 1996 Deactivation of methylrhenium trioxide-peroxide catalysts by diverse and competing pathways J. Am. Chem. Soc. 118 4966 4974 10.1021/ja952305x 1:CAS:528:DyaK28XivVyitLo%3D (Pubitemid 26200971)
23. Y Matusi A Sunouchi T Yamamato 1998 Inhibitory effect of cyclodextrins on the discoloration reaction of an anthocyanide, pelargonidin chloride in acidic media J. Incl. Phenom. Mol. Recognit. Chem. 32 57 67 10.1023/A:1007990418774 (Pubitemid 128142928)
24. F Hapiot S Tilloy E Monflier 2006 Cyclodextrins as supramolecular hosts for organometallic complexes Chem. Rev. 106 767 781 10.1021/cr050576c 1:CAS:528:DC%2BD28Xhs1Citb0%3D
25. Harada, A.: Preparation, properties and stereochemical aspects of inclusion compounds of organometallic complexes with cyclodextrins. In: Zanello, P. (ed.) Chain, Clusters, Inclusion Compounds, Paramagnetic Labels and Organic Rings; Stereochemisty of Organometallic and Inorganic Compounds, vol. 5, pp. 411-455. Elsevier, Amsterdam (1994)
26. MC Ramusino M Bartolomei L Rufini 1996 H-NMR and UV-spectroscopic study of the inclusion complex formation between pyridoxine and β- and γ-cyclodextrin J. Incl. Phenom. Mol. Recognit. Chem. 25 113 116 10.1007/BF01041548 1:CAS:528:DyaK2sXis1Gqtw%3D%3D (Pubitemid 126648433)
27. K Kanagaraj K Pitchumani 2010 Solvent-free multicomponent synthesis of pyranopyrazoles: per-6-amino-β-cyclodextrin as a remarkable catalyst and host Tetrahedron Lett. 51 3312 3316 10.1016/j.tetlet.2010.04.087 1:CAS:528:DC%2BC3cXmsVOisLk%3D
28. S Narayana Murthy B Madhav V Prakash Reddy YVD Nageswar 2010 One-pot synthesis of 2-amino-4H-chromen-4-yl phosphonate derivatives using β-cyclodextrin as reusable catalyst in water Tetrahedron Lett. 51 3649 3653 10.1016/j.tetlet.2010.05.028
29. A Cassez A Ponchel H Bricout S Fourmentin D Landy E Monflier 2006 Eco-efficient catalytic hydrodechlorination of carbon tetrachloride in aqueous cyclodextrin solutions Catal. Lett. 108 209 214 10.1007/s10562-006-0045-7 1:CAS:528:DC%2BD28XktVaquro%3D
30. J Szejtli 1998 Introuction and general over view of cyclodextrin chemistry Chem. Rev. 98 1743 1753 10.1021/cr970022c 1:CAS:528:DyaK1cXksV2itrw%3D (Pubitemid 128633435)
31. AM Al-Ajlouni JH Espenson 1995 Epoxidation of styrenes by hydrogen peroxide as catalyzed by methylrhenium trioxide J. Am. Chem. Soc. 117 9243 9250 10.1021/ja00141a016 1:CAS:528:DyaK2MXns1Cisb4%3D
32. H Eyring 1935 The activated complex in chemical reactions J. Chem. Phys. 3 107 115 10.1063/1.1749604 1:CAS:528:DyaA2MXhs1Sksw%3D%3D
33. AM Al-Ajlouni JH Espenson A Bakac 1993 Reaction of hydrogen peroxide with the oxochromium(IV) ion by hydride transfer Inorg. Chem. 32 3162 3165 10.1021/ic00066a030 1:CAS:528:DyaK3sXkvVWitro%3D
34. AH Gemeay IA Mansour RG El-Sharkawy AB Zaki 2003 Kinetics and mechanism of the heterogeneous catalyzed oxidative degradation of indigo carmine J. Mol. Catal. A Chem. 193 109 120 10.1016/S1381-1169(02)00477-6 1:CAS:528: DC%2BD3sXhsVylsbs%3D