Browse > Article
http://dx.doi.org/10.12925/jkocs.2004.21.1.10

Cycloolefins Oxidation Reaction Catalyzed by Ga(III)-, In(III)- and TI(III)-Porphyrin Derivatives  

Na, Hun-Gil (Department of Chemistry, Daeiin University)
Publication Information
Journal of the Korean Applied Science and Technology / v.21, no.1, 2004 , pp. 76-88 More about this Journal
Abstract
The catalytic oxidation reaction of several cycloolefins in $CH_2Cl_2$ have been investigated using non-redox metalloporphyrin(M = Ga(III), In(III) and TI(III) complexes as a catalyst and sodium hypochlorite as a terminal oxidant. Porphyrins were $(p-CH_3O)$TPP, $(p-CH_3)$TPP, TPP, (p-F)TPP, (p-Cl)TPP and $(F_{20})$TPP (TPP=5,10,15,20-tetraphenyl-21H,23H-porphyrin) and olefins were cyclopentene, cyclohexene, cycloheptene and cyclooctene, The substrate conversion yield(%) was investigated according to the radius effect of non-redox metal ion, substituent effect and hindrance effect of metalloporphyrin. The conversion yield of cycloolefin was in the following order : $C_5$ < $C_6$ < $C_7$ = $C_8$.
Keywords
Ga(III)-; In(III)-; TI(III)-porphyrin; cycloolefin oxidation;
Citations & Related Records
연도 인용수 순위
  • Reference
1 F. Vogtle and E. Weber, 'Host Guest Complex Chemistry Macrocycles' Springer-Verlag, Heidelberg (1985)
2 Y. Watanabe, J. Bio. Inorg, Chem, Commentary, 6, 846 (2001)   DOI   ScienceOn
3 J. E. Huheey, E. A. Keiter, and R. L. Keiter, 'Inorganic Chemistry', 4th ed. Harper Collins College Publishers, New York (1993)
4 K. A. Jorgensen, Chem Rev., 89, 431 (1989)   DOI   ScienceOn
5 K. M. Kadish, J. L. Cornillon, A. Coutsolelosand, and R. Guilard, Inorg. Chem., 26, 4167 (1987)   DOI
6 W. W. Nam and J. S. Valentane, J. Am. Chem Soc, 112, 4977 (1990)   DOI
7 D. D. Perrin and W. L. F. Armago, 'In Purification of Laboratory Chemicals', 3rd ed., Pergamon Press, Oxford (1988)
8 F. Montanari and L. Casella, 'Metalloporphyrins Catalyzed Oxidation', Kluwer Academic Publishers, Dordrecht (1993)
9 D. H. R. Barton, A. E. Martell, and D. T. Sawyer, ' The Activation of Dioxygen and Homogeneous Catalytic Oxidation ' Plenum Press, New York and London (1993)
10 O. Bortolini and B. Meunier, J. Chem. Soc., Chem. Commun., 1364 (1983)
11 K. M. Kadish, B. B. Cocolios, A. Coutsolelos, P. Mitaine, and R. Guilard, Inorg. Chem., 24, 4521 (1985)   DOI
12 B. Meunier, M. Carvalho, 0. Bortolini, and M. Momenteau, Inorg. Chem., 27, 161 (1988)   DOI
13 J. A. Razenberg, R. J. Nolte, and W. M. Drenth, Tetrahedron Lett., 25, 789 (1984)   DOI   ScienceOn
14 J. B. Kim, J. J. Leonard, and F. R. Longo, J. Am. Chem. Soc., 88, 3986 (1972)
15 H. H. Jaffe, Chem Rev., 53, 191 (1953)   DOI
16 D. H. Mcdaniel and H. C. Brown, J. Ors. Chem., 23, 420 (1958)   DOI
17 B. R. James, 'Homogeneous Hydrogenation', Wiley Interscience, New York (1973)
18 A. Yamamoto, 'Organotransition Metal Chemistry' Wiley Interscience, New York (1986)
19 H. Yoon, Y. R. Wagler. K. J. Connor, and C. J. Burrows, J. Am. Chem. Soc., 112, 4568 (1990)   DOI