View Item 

Show simple item record

Metalloporphyrins in Oxidative Catalysis. Oxygen Transfer Reactions of Oxochromium Porphyrins
dc.contributor.authorGroves, John T.en_US
dc.contributor.authorKruper, William J.en_US
dc.date.accessioned2013-12-04T18:58:16Z
dc.date.available2013-12-04T18:58:16Z
dc.date.issued1985en_US
dc.identifier.citationGroves, John T.; Kruper, William J. (1985). "Metalloporphyrins in Oxidative Catalysis. Oxygen Transfer Reactions of Oxochromium Porphyrins." Israel Journal of Chemistry 25(2): 148-154. <http://hdl.handle.net/2027.42/101881>en_US
dc.identifier.issn0021-2148en_US
dc.identifier.issn1869-5868en_US
dc.identifier.urihttps://hdl.handle.net/2027.42/101881
dc.description.abstractThe oxidation of chloro‐5‐10,15,20‐tetramesitylporphyrinotoiron(III) with peroxyacids affords a reactive oxoiron(IV)‐porphyrin cation radical species 2. The characterization of 2 and its oxochromium analogs 3, 4 and 5 are reviewed. The nature of reactive oxochromium species derived from chromyl reagents is also reviewed. The oxidation of triphenylphosphine by CrOTPP (11), CrOTTP (13) and CrOTMP (14) is described. Variations in the rate constants indicate that steric factors affect the rate of oxygen atom transfer. Activation parameters for the oxidation of triphenylphosphine by 14 are ΔH ≠ = 6.96 kcal/mol and ΔS ≠ = −39 eu. The oxidation of t ‐butylphenylcarbinol (18) by CrOTPP gave predominantly benzaldehyde via carbon—carbon bond cleavage while the chromium(III) porphyrin‐catalyzed oxidation of 18 by iodosylbenzene afforded t ‐butylphenylketone.en_US
dc.publisherWILEY‐VCH Verlagen_US
dc.titleMetalloporphyrins in Oxidative Catalysis. Oxygen Transfer Reactions of Oxochromium Porphyrinsen_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelChemistryen_US
dc.subject.hlbtoplevelScienceen_US
dc.description.peerreviewedPeer Revieweden_US
dc.contributor.affiliationumDepartment of Chemistry, The University of Michigan, Ann Arbor, MI 48109 USAen_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/101881/1/198500023_ftp.pdf
dc.identifier.doi10.1002/ijch.198500023en_US
dc.identifier.sourceIsrael Journal of Chemistryen_US
dc.identifier.citedreferencea. S. Sarkan and J.P. Singh, J. Chem. Soc., Chem. Commun., 509 ( 1974 ). b. C.J. Willis, J. Chem. Soc., Chem. Commun., 945 ( 1972 ). c. M. Krumpole and J. Rocek, J. Am. Chem. Soc., 101, 3206 ( 1979 ).en_US
dc.identifier.citedreferenceJ.T. Groves and R.C. Haushalter, J. Chem. Soc., Chem. Commun., 1155 – 1156 ( 1981 ).en_US
dc.identifier.citedreferencea. J.T. Groves, W.J. Kruper, Jr., R.C. Haushalter and W.M. Butler, Inorg. Chem., 21, 1363 – 1368 ( 1982 ). b. T. Takahashi,unpublished results. c. J.R. Budge, B.M.K. Gatehouse, M.C. Nesbit and B.O. West, J. Chem. Soc., Chem. Commun., 370 ( 1981 ).en_US
dc.identifier.citedreferencea. J.T. Groves, T. Takahashi and W.M. Butler, Inorg. Chem., 22, 884 – 887 ( 1983 ). b. J.W. Buchler, C. Dreher, K.L. Lay, A. Raap and K. Gersonde, Inorg. Chem., 22, 879 – 884 ( 1983 ).en_US
dc.identifier.citedreferencea. J. Hampton, A. Leo and F.J. Westheimer, J. Org. Chem., 78, 306 ( 1956 ). b. J. Rocek and A.E. Radkowsky, J. Am. Chem. Soc., 90, 2986 ( 1968 ). c. J. Rocek and A.E. Radkowski, J. Am. Chem. Soc., 95, 7123 ( 1973 ). d. K.B. Wiberg and S.K. Mukherjee, J. Am. Chem. Soc., 96, 1884 ( 1974 ). e. K.B. Wiberg and S.K. Mukherjee, J. Am. Chem. Soc., 96, 6647 ( 1974 ). f. P.M. Nave and W.S. Trahanovsky, J. Am. Chem. Soc., 92, 1120 ( 1970 ).en_US
dc.identifier.citedreferencea. K.B. Wiberg and G. Foster, J. Am. Chem. Soc., 83, 423 ( 1961 ). b. R.H. Eastman and R.A. Quinn, J. Am. Chem. Soc., 82, 4249 ( 1960 )., c. K.B. Wiberg and A.S. Fox, J. Am. Chem. Soc., 85, 3487 ( 1963 ). d. C.N. Rentea, M. Rentea, I. Necsoiv and C.D. Nonitzesco, Tetrahedron, 24, 4667 ( 1968 ).en_US
dc.identifier.citedreferencea. S. Ramesh, S.N. Mahapatro, J.H. Liu and J. Rocek, J. Am. Chem. Soc., 103, 5172 ( 1981 ). b. S.N. Mahapatro, M. Krumpole and J. Rocek, J. Am. Chem. Soc., 102, 3799 ( 1980 ).en_US
dc.identifier.citedreferencea. K.R. Seddon and Y.H. Thomas, Inorg. Chem., 17, 749 ( 1978 ). b. G.D. Garner, J. Kendrick, P. Lambert, F.E. Mabbs and I.H. Hillier, Inorg. Chem., 15, 1287 ( 1976 ). c. O.V. Ziebarth and J. Selbin, J. Inorg. Nucl. Chem., 32, 849 ( 1970 ).en_US
dc.identifier.citedreferencea. H. Kon, J. Inorg. Nucl. Chem., 25, 933 ( 1963 ). b. M. Krumpole, B.G. DeBoer and J. Rocek, J. Am. Chem. Soc., 100, 145 ( 1978 ). c. F. Freeman, C.R. Armstead, M.G. Essig, E.M. Karchefski, C.J. Kojima, V.C. Manopoli and A.H. Wickman, J. Chem. Soc., Chem. Commun., 65 ( 1980 ).en_US
dc.identifier.citedreferenceK.B. Sharpless, A.Y. Teranishi and J.E. Bäckvall, J. Am. Chem. Soc., 99, 3120 – 3128 ( 1977 ).en_US
dc.identifier.citedreferencea. A.K. Rappé and W.A. Goddard, III, J. Am. Chem. Soc., 102, 5114 – 5115 ( 1980 ). b. A.K. Rappé and W.A. Goddard, III, J. Am. Chem. Soc., 104, 448 – 456 ( 1982 ).en_US
dc.identifier.citedreferenceD.M. Walba, C.H. DePuy, J.J. Grabowski and V.M. Bierbaum, Organometallics, 3, 498 – 499 ( 1984 ).en_US
dc.identifier.citedreferenceN. Miyaura and J. Kochi, J. Am. Chem. Soc., 105, 2368 – 2378 ( 1983 ).en_US
dc.identifier.citedreferencea. D.H. Chin, A.L. Balch and G.N. La Mar, J. Am. Chem. Soc., 102, 1446 – 1448 ( 1980 ). b. D.H. Chin, G.N. La Mar and A.L. Balch, J. Am. Chem. Soc., 102, 4344 – 4350 ( 1980 ).en_US
dc.identifier.citedreferencea. J.T. Groves and T.E. Nemo, J. Am. Chem. Soc., 105, 5876 – 5791 ( 1983 ). b. J.T. Groves and T.E. Nemo, J. Am. Chem. Soc., 105, 6243 – 6248 ( 1983 ). c. J.T. Groves and R.S. Myers, J. Am. Chem. Soc., 105, 5791 – 5796 ( 1983 ).en_US
dc.identifier.citedreferenceComplications of this interpretation arise if long range electron transfer occurs between the approaching nucleophile and the metal oxide.en_US
dc.identifier.citedreferenceW.J. Kruper, Jr. Ph.D. Thesis, University of Michigan, 1982.en_US
dc.identifier.citedreferencea. H. Ledon, F. Varescon, T. Malinski and K.M. Kadish, Inorg. Chem., 23, 263 – 268 ( 1984 ). b. H. Ledon and M. Bonnet, J. Mol. Catal., 2, 309 ( 1980 ).en_US
dc.identifier.citedreferencea. F.P. Guengerich and T.L. Macdonald, Acc. Chem. Res., 17, 9 – 16 ( 1984 ). b. R.E. White and M.J. Coon, Ann. Rev. Biochem., 49, 315 ( 1980 ). c. V. Ullrich, Top. Curr. Chem., 83, 67 – 104 ( 1979 ). d. J.T. Groves, Adv. Inorg. Biochem., 119 – 145 ( 1979 ).en_US
dc.identifier.citedreferencea. F.F. Kadlubar, K.C. Morton and D.M. Ziegler, Biochem. Biophys. Res. Commun., 54, 1255 – 1261 ( 1973 ). b. A.D. Rahimtula and P.J. O'Brien, Biochem. Biophys. Res. Commun., 60, 440 – 447 ( 1974 ). E.G. Hrycay and P.J. O'Brien, Arch. Biochem. Biophys., 152, 480 – 494 ( 1972 ). c. G.D. Nordblom, R.E. White and M.J. Coon, Arch. Biochem. Biophys., 175, 524 – 533 ( 1976 ). d. E.G. Hrycay, J.A. Gustafsson, M. Ingelman‐Sundberg and L. Ernster, Biochem. Biophys. Res. Commun., 66, 290 – 296 ( 1975 ). e. F. Lichtenberger, W. Nastainczyk and V. Ullrich, Biochem. Biophys. Res. Commun., 70, 939 – 946 ( 1976 ).en_US
dc.identifier.citedreferencea. A. Wolberg and J. Manassen, J. Am. Chem. Soc., 92, 2982 – 2991 ( 1970 ). b. H.B. Dunford and J.S. Stillman, Coord. Chem. Rev., 19, 187 – 251 ( 1976 ). c. W.D. Hewson and L.P. Hager in D. Dolphin, ed., The Porphyrins,Vol. VIII, Academic Press, New York, 1979,pp. 295 – 332.en_US
dc.identifier.citedreferenceJ.T. Groves and G.A. McClusky, J. Am. Chem. Soc., 98, 859 ( 1976 ).en_US
dc.identifier.citedreferencea. J.T. Groves, T.E. Nemo and R.S. Myers, J. Am. Chem. Soc., 101, 1032 – 1033 ( 1979 ). b. J.T. Groves and W.J. Kruper, Jr., J. Am. Chem. Soc., 101, 7613 – 7614 ( 1979 ).en_US
dc.identifier.citedreferencea. C.K. Chang and M.‐J. Kuo, J. Am. Chem. Soc., 101, 3413 – 3415 ( 1973 ). b. C.K. Chang and F. Ebina, J. Chem. Soc., Chem. Commun., 778 ( 1981 ). c. J.R. Lindsay‐Smith and P.R. Sleath, J. Chem. Soc., Perkin Trans. 2, 1009 – 1015 ( 1982 ). d. D. Dolphin, B.R. James and T. Leung, Inorg. Chim. Acta, 79, 25 – 27 ( 1983 ). e. D. Mansuy, J.F. Bartoli, J.C. Chottard and M. Lange, Angew. Chem., Int. Ed. Engl., 19, 909 ( 1980 ). f. D. Mansuy, M. Fontecane and J.F. Bartoli, J. Chem. Soc., Chem. Commun., 253 ( 1983 ). g. C.L. Hill and B.C. Schardt, J. Am. Chem. Soc., 102, 6374 – 6375 ( 1980 ). h. C.L. Hill, J.A. Smegal and T.J. Henly, J. Org. Chem., 48, 3277 – 3281 ( 1983 ). i. I. Tabushi and A. Yazaki, J. Am. Chem. Soc., 103, 7371 – 7372 ( 1981 ). j. H.J. Ledon, P. Durbut and F. Varescon, J. Am. Chem. Soc., 103, 3601 – 3602 ( 1981 ). k. M.W. Nee and T.C. Bruice, J. Am. Chem. Soc., 104, 6123 – 6125 ( 1982 ). l. E. Guilmet and B. Munier, Tetrahedron Lett., 4449 – 4452 ( 1980 ). m. M.‐E. De Carvalho and B. Munier, Tetrahedron Lett., 24, 3621 – 3624 ( 1983 ).en_US
dc.identifier.citedreferenceJ.T. Groves, R.C. Haushalter, M. Nakamura, T.E. Nemo and B.J. Evans, J. Am. Chem. Soc., 103, 2884 – 2886 ( 1981 ).en_US
dc.identifier.citedreferencea. B. Boso, G. Lang, T.J. McMurry and J.T. Groves, J. Chem. Phys., 79, 1122 – 1126 ( 1983 ). b. J.E. Penner‐Hahn, T.J. McMurry, M. Renner, L. Latos‐Graznysky, K.S. Eble, I.M. Davis, A.L. Balch, J.T. Groves, J.H. Dawson and K.O. Hodgson, J. Biol. Chem., 258, 12761 – 12764 ( 1983 ).en_US
dc.identifier.citedreferenceM. Nakamura and T.J. McMurry,unpublished results.en_US
dc.identifier.citedreferenceC.‐S. Kim and R.K. Murmann, Inorg. Chem., 23, 263 – 268 ( 1984 )and references cited therein.en_US
dc.owningcollnameInterdisciplinary and Peer-Reviewed


Files in this item

Name:
198500023_ftp.pdf
Size:
863.4KB
Format:
PDF
View/Open

Show simple item record

Remediation of Harmful Language

The University of Michigan Library aims to describe its collections in a way that respects the people and communities who create, use, and are represented in them. We encourage you to Contact Us anonymously if you encounter harmful or problematic language in catalog records or finding aids. More information about our policies and practices is available at Remediation of Harmful Language.

Accessibility

If you are unable to use this file in its current format, please select the Contact Us link and we can modify it to make it more accessible to you.