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Synthesis, electrochemistry, and structural properties of porphyrins with metal-carbon single bonds and metal-metal bonds

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Metal Complexes with Tetrapyrrole Ligands I

Part of the book series: Structure and Bonding ((STRUCTURE,volume 64))

Abstract

Porphyrins are known to coordinate with most of the metallic or pseudo-metallic elements. However, in spite of the large number of isolated metalloporphyrin derivatives, metal-carbon σ-bonded complexes are limited only to the following series: Fe, Ru, Co, Rh, Ir, Ti, Al, Ga, In, Tl, Si, Ge, Sn, and Zn.

These complexes are of great interest as model compounds for understanding the functions and relationships of several biological macromolecules, as well as for their chemical reactivity. In the latter case the insertion of small molecules between the metal ion and the carbon atom may result in activation of the inserted molecule or may generate new monomeric or polymeric materials. In addition, metal-carbon σ-bonded porphyrins can act as precursors in the synthesis of metal-metal bonded derivatives.

This review will cover the general strategies for synthesizing organometallic porphyrin complexes. Furthermore, we will also discuss the electrochemical and structural properties of metalloporphyrins from the viewpoint of organometallic chemistry. In doing this we will focus on the following points:

  1. (i)

    We will give a summary of the synthetic procedures and characteristics of metal-alkyl (aryl) σ-bonded porphyrins. Special emphasis will be placed on the magnetic properties of the ironcarbon porphyrin derivatives.

  2. (ii)

    The insertion of carbon dioxide and sulfur dioxide into the metal-carbon bond of metalloporphyrins containing main group metals such as Ga, In, and Al will be discussed.

  3. (iii)

    The synthesis of metal-metal bonded metalloporphyrins containing a σ-bond or a donor-acceptor bond will be presented; we will also focus on the structural and electrochemical properties of some typical compounds.

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References

  1. Mansuy, D., Nastainczyk, W., Ullrich, V.: Arch. Pharmakol. 285, 315 (1974)

    Google Scholar 

  2. Ullrich, V.: Top. Curr. Chem. 83, 68 (1979)

    Google Scholar 

  3. Ortiz de Montellano, P. R. (ed.): Cytochrome P-450: Structure, Mechanism, and Biochemistry, Plenum Press, New York 1986

    Google Scholar 

  4. Mansuy, D., Lange, M., Chottard, J. C., Bartoli, J. F., Chevrier, B., Weiss, R.: Ang. Chem. Int. Ed. Engl. 17, 781 (1978)

    Google Scholar 

  5. Augusto, O., Kunze, K. L., Ortiz de Montellano, P. R.: J. Biol. Chem. 257, 6231 (1982)

    Google Scholar 

  6. Saito, S., Hano, H. A.: Proc. Natl. Acad. Sci. USA 78, 5508 (1981)

    Google Scholar 

  7. Ortiz de Montellano, P. R., Kunze, K. L.: J. Am. Chem. Soc. 103, 6334 (1981)

    Google Scholar 

  8. Miller, J. S. (ed.): Extended Linear Chain Compounds, New York, Plenum Press 1982

    Google Scholar 

  9. Clarke, D. A., Grigg, R., Johnson, A. W.: J. Chem. Soc., Chem. Commun. 208 (1966)

    Google Scholar 

  10. Clarke, D. A., Dolphin, D., Grigg, R., Johnson, A. W., Pinnock, H. A.: J. Chem. Soc. C, 881 (1968)

    Google Scholar 

  11. Reed, C. A., Mashiko, T., Bentley, S. P., Kastner, M. E., Scheidt, W. R., Spartalian, K., Lang, G.: J. Am. Chem. Soc. 101, 2948 (1979)

    Google Scholar 

  12. Ortiz de Montellano, P. R., Kunze, K. L., Augusto, A.: ibid. 104, 3545 (1982)

    Google Scholar 

  13. Cocolios, P., Laviron, E., Guilard, R.: J. Organomet. Chem. 228, C39 (1982)

    Google Scholar 

  14. Ogoshi, H., Sugimoto, H., Yoshida, Z., Kobayashi, H., Sakai, H., Maeda, Y.: ibid. 234, 185 (1982)

    Google Scholar 

  15. Mansuy, D., Battioni, J. P.: J. Chem. Soc., Chem. Commun., 638 (1982)

    Google Scholar 

  16. Cocolios, P., Lagrange, G., Guilard, R.: J. Organomet. Chem. 253, 65 (1983)

    Google Scholar 

  17. Battioni, J. P., Lexa, D., Mansuy, D., Savéant, J. M.: J. Am. Chem. Soc. 105, 207 (1983)

    Google Scholar 

  18. Ogoshi, H., Setsune, J., Omura, T., Yoshida, Z.: ibid. 97, 6461 (1975)

    Google Scholar 

  19. Latour, J. M., Boreham, C. J., Marchon, J. C.: J. Organomet. Chem. 190, C61 (1980)

    Google Scholar 

  20. Ogoshi, H., Setsune, J., Yoshida, Z.: ibid. 159, 317 (1978)

    Google Scholar 

  21. Coutsolelos, A., Guilard, R.: ibid. 253, 273 (1983)

    Google Scholar 

  22. Guilard, R., Cocolios, P., Fournari, P.: ibid. 129, C11 (1977)

    Google Scholar 

  23. Cocolios, P., Guilard, R., Fournari, P.: ibid. 179, 311 (1979)

    Google Scholar 

  24. Tabard, A., Zrineh, A., Guilard, R., Kadish, K. M.: Inorg. Chem. in press (1987)

    Google Scholar 

  25. Kadish, K. M., Xu, Q. Y., Barbe, J. M., Guilard, R.: submitted for publication

    Google Scholar 

  26. Maskasky, J. E., Kenney, M. E.: J. Am. Chem. Soc. 93, 2060 (1971)

    Google Scholar 

  27. Maskasky, J. E., Kenney, M. E.: ibid. 93, 1443 (1973)

    Google Scholar 

  28. Miyamoto, T. K., Hasegawa, T., Takagi, S., Sasaki, Y.: Chem. Lett. 1181 (1983)

    Google Scholar 

  29. Miyamoto, T. K., Sugita, N., Matsumoto, Y., Sasaki, Y., Konno, M.: ibid. 1695 (1983)

    Google Scholar 

  30. Cloutour, C., Lafargue, D., Richards, J. A., Pommier, J. C.: J. Organomet. Chem. 137, 157 (1977)

    Google Scholar 

  31. Cloutour, C., Lafargue, D., Pommier, J. C.: ibid. 161, 327 (1978)

    Google Scholar 

  32. Barbe, J. M., Guilard, R.: unpublished results

    Google Scholar 

  33. Clarke, D. A., Grigg, R., Johnson, A. W., Pinnock, H. A.: J. Chem. Soc., Chem. Commun. 309 (1967)

    Google Scholar 

  34. Momenteau, M., Fournier, M., Rougee, M.: J. Chim. Phys. 67, 926 (1970)

    Google Scholar 

  35. Perree-Fauvet, M., Gaudemer, A., Boucly, P., Devynck, J.: J. Organomet. Chem. 120, 439 (1976)

    Google Scholar 

  36. Kadish, K. M., Tabard, A.: unpublished results

    Google Scholar 

  37. Ogoshi, H., Watanabe, E., Koketsu, N., Yoshida, Z.: Bull. Chem. Soc. Jpn. 49, 2529 (1976)

    Google Scholar 

  38. Dolphin, D., Halko, D. J., Johnson, E.: Inorg. Chem. 20, 4348 (1981)

    Google Scholar 

  39. Ogoshi, H., Omura, T., Yoshida, Z.: J. Am. Chem. Soc. 95, 1666 (1973)

    Google Scholar 

  40. Ogoshi, H., Setsune, J., Yoshida, Z.: ibid. 99, 3869 (1977)

    Google Scholar 

  41. Ogoshi, H., Setsune, J., Nanbo, Y., Yoshida, Z.: J. Organomet. Chem. 159, 329 (1978)

    Google Scholar 

  42. Lexa, D., Mispelter, J., Savéant, J. M.: J. Am. Chem. Soc. 103, 6806 (1981)

    Google Scholar 

  43. Lexa, D., Savéant, J. M.: ibid. 104, 3503 (1982)

    Google Scholar 

  44. Grigg, R., Trocha-Grimshaw, J., Viswanatha, V.: Tetrahedron Lett. 4, 289 (1976)

    Google Scholar 

  45. Abeysekera, A. M., Grigg, R., Trocha-Grimshaw, J., Viswanatha, V.: ibid. 36, 3189 (1976)

    Google Scholar 

  46. Abeysekera, A. M., Grigg, R., Trocha-Grimshaw, J., Viswanatha, V.: J. Chem. Soc., Chem. Commun. 227 (1976)

    Google Scholar 

  47. Abeysekera, A. M., Grigg, R., Trocha-Grimshaw, J., Viswanatha, V.: J. Chem. Soc., Perkin I, 1395 (1977)

    Google Scholar 

  48. Parshall, G. W., Mrowea, J. J.: Adv. in Organomet. Chem. 7, 157 (1968)

    Google Scholar 

  49. Brault, D., Bizet, C., Morlière, P., Rougee, M., Land, E. J., Santus, R., Shallow, A. J.: J. Am. Chem. Soc. 102, 1015 (1980)

    Google Scholar 

  50. Brault, D., Neta, P.: ibid. 103, 2705 (1981)

    Google Scholar 

  51. Callot, H. J., Schaeffer, E.: J. Organomet. Chem. 145, 91 (1978)

    Google Scholar 

  52. Callot, H. J., Schaeffer, E.: J. Chem. Soc., Chem. Commun., 937 (1978)

    Google Scholar 

  53. Callot, H. J., Schaeffer, E.: Nouv. J. Chim. 4, 311 (1980)

    Google Scholar 

  54. Callot, H. J., Schaeffer, E.: J. Organomet. Chem. 193, 111 (1980)

    Google Scholar 

  55. Cohen, J. A., Chow, B. C.: Inorg. Chem. 13, 488 (1974)

    Google Scholar 

  56. Wayland, B. B., Woods, B. A.: J. Chem. Soc., Chem. Commun., 700 (1981)

    Google Scholar 

  57. Paonessa, R. S., Thomas, N. C., Halpern, J.: J. Am. Chem. Soc. 107, 4333 (1985)

    Google Scholar 

  58. Inoue, S., Takeda, N.: Bull. Chem. Soc. Jpn. 50, 984 (1977)

    Google Scholar 

  59. Takeda, N., Inoue, S.: ibid. 51, 3564 (1978)

    Google Scholar 

  60. Henrick, K., Matthews, R. W., Tasker, P. A.: Inorg. Chem. 16, 3293 (1977)

    Google Scholar 

  61. Brady, F., Henrick, K., Matthews, R. W.: J. Organomet. Chem. 210, 281 (1981)

    Google Scholar 

  62. Inoue, S., Murayama, H., Takeda, N., Ohkatsu, Y.: Chem. Lett., 317 (1982)

    Google Scholar 

  63. Collman, J. P., McElwee-White, L., Brothers, P. J., Rose, E.: J. Am. Chem. Soc. 107, 6110 (1985)

    Google Scholar 

  64. Collman, J. P., Prodolliet, J. W., Leidner, C. R.: ibid. 108, 2916 (1986)

    Google Scholar 

  65. Ratti, C., Guilard, R.: unpublished results

    Google Scholar 

  66. Kadish, K. M., Boisselier-Cocolios, B., Cocolios, P., Guilard, R.: Inorg. Chem. 24, 2139 (1985)

    Google Scholar 

  67. Kadish, K. M., Boisselier-Cocolios, B., Coutsolelos, A., Mitaine, P., Guilard, R.: ibid. 24, 4521 (1985)

    Google Scholar 

  68. Tabard, A., Cocolios, P., Lagrange, G., Gerardin, R., Hubsch, J., Lecomte, C., Zarembowitch, J., Guilard, R.: submitted for publication

    Google Scholar 

  69. Scheidt, W. R., Reed, C. A.: Chem. Rev. 81, 543 (1981)

    Google Scholar 

  70. Mitra, S.: Magnetic Susceptibility of Iron Porphyrins, Part. II, in: Iron Porphyrins (eds. Lever, A. B. P., Gray, H. B.), p. 1, Reading MA, Addison-Wesley 1983

    Google Scholar 

  71. Guilard, R., Boisselier-Cocolios, B., Tabard, A., Cocolios, P., Simonet, B., Kadish, K. M.: Inorg. Chem. 24, 2509 (1985)

    Google Scholar 

  72. La Mar, G. N., Walker, F. A.: Nuclear Magnetic Resonance of Paramagnetic Metalloporphyrins in: The Porphyrins, Vol. IV (ed. Dolphin, D.), p. 61, New York, Academic Press 1979

    Google Scholar 

  73. Tabard, A., Lagrange, G., Guilard, R., Jouan, M., Dao, N. Q.: J. Organomet. Chem. 308, 335 (1986)

    Google Scholar 

  74. Slichter, L. P., Drickamer, H. G.: J. Chem. Phys. 56, 2142 (1972)

    Google Scholar 

  75. La Mar, G. N., Eaton, G. R., Holm, R. H., Walker, F. A.: J. Am. Chem. Soc. 95, 63 (1973)

    Google Scholar 

  76. Cervone, E., Camassel, F. D., Luciani, M. L., Furlani, C.: J. Inorg. Nucl. Chem. 31, 1101 (1969)

    Google Scholar 

  77. Lang, G.: Applied Physics 38, 915 (1967)

    Google Scholar 

  78. Geiger, D. K., Scheidt, W. R.: Inorg. Chem. 23, 1970 (1984)

    Google Scholar 

  79. Reed, C. A.: Iron (I) and Iron (IV) Porphyrins, in: Electrochemical and Spectroelectrochemical Studies of Biological Redox Components (ed. Kadish, K. M.), p. 333, Washington, American Chemical Soc. 1982

    Google Scholar 

  80. LanÇon, D., Cocolios, P., Guilard, R., Kadish, K. M.: J. Am. Chem. Soc. 106, 4472 (1984)

    Google Scholar 

  81. LanÇon, D., Cocolios, P., Guilard, R., Kadish, K. M.: Organometallics 3, 1164 (1984)

    Google Scholar 

  82. Kadish, K. M., LanÇon, D., Cocolios, P., Guilard, R.: Inorg. Chem. 23, 2372 (1984)

    Google Scholar 

  83. Guilard, R., Lagrange, G., Tabard, A., LanÇon, D., Kadish, K. M.: ibid. 24, 3649 (1985)

    Google Scholar 

  84. Callot, H. J., Cromer, R., Louati, A., Gross, M.: Nouv. J. Chim. 8, 765 (1985)

    Google Scholar 

  85. Callot, H. J., Metz, F., Cromer, R.: ibid. 8, 759 (1984)

    Google Scholar 

  86. Kadish, K. M., Yao, C. L., Anderson, J. E., Cocolios, P.: Inorg. Chem. 24, 4515 (1985)

    Google Scholar 

  87. Kadish, K. M., Anderson, J. E., Yao, C. L., Guilard, R.: ibid. 25, 1277 (1986)

    Google Scholar 

  88. Anderson, J. E., Yao, C. L., Kadish, K. M.: ibid. 25, 718 (1986)

    Google Scholar 

  89. Anderson, J. E., Yao, C. L., Kadish, K. M.: J. Am. Chem. Soc. 109, 1106 (1987)

    Google Scholar 

  90. Anderson, J. E., Yao, C. L., Kadish, K. M.: Organometallics 6, 706 (1987)

    Google Scholar 

  91. Yao, C. L.: PhD Thesis, University of Houston (1987)

    Google Scholar 

  92. Sugimoto, H., Ueda, N., Mori, M.: J. Chem. Soc., Dalton Trans., 1611 (1982)

    Google Scholar 

  93. Cornillon, J. L., Anderson, J. E., Swistak, C., Kadish, K. M.: J. Am. Chem. Soc. 108, 7633 (1986)

    Google Scholar 

  94. Tabard, A., Guilard, R., Kadish, K. M.: Inorg. Chem. 25, 4277 (1986)

    Google Scholar 

  95. Kadish, K. M., Xu, Q. Y., Barbe, J. M., Anderson, J. E., Wang, E., Guilard, R., submitted for publication

    Google Scholar 

  96. Kadish, K. M., Cornillon, J. L., Cocolios, P., Tabard, A., Guilard, R.: Inorg. Chem. 24, 3645 (1985)

    Google Scholar 

  97. Momenteau, M., Loock, B.: J. Mol. Catal. 7, 315 (1980)

    Google Scholar 

  98. Momenteau, M., Loock, B., Larollette, D., Tetreau, C., Mispelter, J.: J. Chem. Soc., Chem. Commun., 962 (1983)

    Google Scholar 

  99. Kadish, K. M.: J. Electroanal. Chem. 168, 261 (1984)

    Google Scholar 

  100. Doppelt, P.: Inorg. Chem. 23, 4009 (1984)

    Google Scholar 

  101. Furhrhop, J. H.: Redox reactions of metalloporphyrins, in: Structure and Bonding, Vol. 18, Chapter 1, pp. 1–68, New York, Springer 1974

    Google Scholar 

  102. Loew, G. H.: Theoretical investigations of iron porphyrins, in: Iron Porphyrins (eds. Lever, A. B. P., Gray, H. P.), Part I, Chapter 1, pp. 1–87, Reading, Mass., Addison-Wesley 1983

    Google Scholar 

  103. Lagrange, G., Cocolios, P., Guilard, R.: J. Organomet. Chem. 260, C16 (1984)

    Google Scholar 

  104. Felton, R. H., Linschitz, H.: J. Am. Chem. Soc. 88, 1113 (1966)

    Google Scholar 

  105. Walker, F. A., Beroiz, D., Kadish, K. M.: ibid. 98, 3484 (1976)

    Google Scholar 

  106. Cloutour, C., Lafargue, D., Pommier, J. C.: J. Organomet. Chem. 190, 35 (1980)

    Google Scholar 

  107. Takeda, A., Syal, S. K., Sasada, Y., Omura, T., Ogoshi, H., Yoshida, Z. Y.: Acta Cryst. B32, 62 (1976)

    Google Scholar 

  108. Fleischer, E. B., Lavallee, D.: J. Am. Chem. Soc. 89, 7132 (1967)

    Google Scholar 

  109. Lecomte, C., Protas, J., Cocolios, P., Guilard, R.: Acta Cryst. B36, 2769 (1980)

    Google Scholar 

  110. Colin, J., Chevrier, B.: Organometallics 4, 1090 (1985)

    Google Scholar 

  111. Troughton, P. G. H., Skapski, A. C.: J. Chem. Soc., Chem. Commun., 575 (1968)

    Google Scholar 

  112. Churchill, M. R.: Inorg. Chem. 4, 1734 (1965)

    Google Scholar 

  113. Churchill, M. R.: Perfect. Struct. Chem. 3, 91 (1970)

    Google Scholar 

  114. Buchler, J. W., Kokisch, W., Smith, P. D.: Struct. Bonding 34, 79 (1978)

    Google Scholar 

  115. Scheidt, W. R., Lee, Y. L., Hatano, K.: Inorg. Chim. Acta, Bioinorg. Chem. 79, 192 (1983)

    Google Scholar 

  116. Scheidt, W. R., Frisse, M. E.: J. Am. Chem. Soc. 97, 17 (1975)

    Google Scholar 

  117. Hoard, J. L.: Stereochemistry of Porphyrins and Metalloporphyrins, in: Porphyrins and Metalloporphyrins (ed. Smith, K. M.), p. 317, Elsevier, Amsterdam 1975

    Google Scholar 

  118. Chevrier, B., Weiss, R., Lange, M., Chottard, J. C., Mansuy, D.: J. Am. Chem. Soc. 103, 2899 (1981)

    Google Scholar 

  119. Ball, R. G., Lee, K. M., Marshall, A. G., Trotter, J.: Inorg. Chem. 19, 1463 (1980)

    Google Scholar 

  120. Cullen, D. L., Meyer, E. F. Jr., Smith, K. M.: ibid. 16, 1179 (1977)

    Google Scholar 

  121. Hoard, J. L., Cohen, G. H., Glick, M. D.: J. Am. Chem. Soc. 89, 1992 (1967)

    Google Scholar 

  122. Lecomte, C., Protas, J., Guilard, R., Fournari, P.: J. Chem. Soc., Chem. Commun., 434 (1976)

    Google Scholar 

  123. Lecomte, C., Protas, J., Guilard, R., Fliniaux, B., Fournari, P.: J. Chem. Soc., Dalton Trans., 1306 (1979)

    Google Scholar 

  124. Lecomte, C., Protas, J., Richard, P., Barbe, J. M., Guilard, R.: ibid., 247 (1982)

    Google Scholar 

  125. Diebold, T., Chevrier, B., Weiss, R.: Inorg. Chem. 18, 1193 (1979)

    Google Scholar 

  126. Colin, J., Butler, G., Weiss, R.: ibid. 19, 3829 (1980)

    Google Scholar 

  127. Cocolios, P., Guilard, R., Bayeul, D., Lecomte, C.: ibid. 24, 2058 (1985)

    Google Scholar 

  128. Oumous, H., Lecomte, C., Protas, J., Cocolios, P., Guilard, R.: Polyhedron 3, 651 (1984)

    Google Scholar 

  129. Buchler, J. W.: Static Coordination Chemistry of Metalloporphyrins, in: Porphyrins and Metalloporphyrins (ed. Smith, K. M.), p. 157, Amsterdam, Elsevier 1975

    Google Scholar 

  130. Aida, T., Inoue, S.: J. Am. Chem. Soc. 105, 1304 (1983)

    Google Scholar 

  131. Vitzthum, G., Lindner, E.: Angew. Chem., Int. Ed. Engl. 10, 315 (1971)

    Google Scholar 

  132. Guilard, R., Cocolios, P., Fournari, P., Lecomte, C., Protas, J.: J. Organomet. Chem. 168, C49 (1979)

    Google Scholar 

  133. Cocolios, P., Fournari, P., Guilard, R., Lecomte, C., Protas, J., Boubel, J. C.: J. Chem. Soc., Dalton Trans., 2081 (1980)

    Google Scholar 

  134. Boukhris, A., Lecomte, C., Coutsolelos, A., Guilard, R.: J. Organomet. Chem. 303, 151 (1986)

    Google Scholar 

  135. Cocolios, P., Lagrange, G., Guilard, R., Oumous, H., Lecomte, C.: J. Chem. Soc., Dalton Trans., 567 (1984)

    Google Scholar 

  136. Philippi, M. A., Baenzinger, N., Goff, H. M.: Inorg. Chem. 20, 3904 (1981)

    Google Scholar 

  137. Kitching, W., Fong, C. W.: Organomet. Chem. Rev. A5, 281 (1970)

    Google Scholar 

  138. Wojcicki, A.: Adv. Organomet. Chem. 12, 31 (1974)

    Google Scholar 

  139. Deakon, G. B., Felder, P. W.: Aust. J. Chem. 22, 549 (1969)

    Google Scholar 

  140. Cocolios, P.: Thèse de Doctorat d'Etat, p. 154, Dijon, France 1982

    Google Scholar 

  141. Mays, M. J., Bailey, J.: J. Chem. Soc., Dalton Trans., 578 (1977)

    Google Scholar 

  142. Olapinski, H., Weidlein, J., Hausen, H. D.: J. Organomet. Chem. 64, 193 (1974)

    Google Scholar 

  143. Palmer, G.: Electron Paramagnetic Resonance of Hemoproteins, in: The Porphyrins, Vol. IV (ed. Dolphin, D.), p. 313, New York, Academic Press 1979

    Google Scholar 

  144. Oumous, H.: Thèse de Troisième Cycle, p. 58, Nancy, France 1983

    Google Scholar 

  145. Buchler, J. W.: Synthesis and Properties of Metalloporphyrins, in: The Porphyrins, Vol. I (ed. Dolphin, D.), p. 389, New York, Academic Press 1978

    Google Scholar 

  146. Gouterman, M.: Electronic Spectra, in: The Porphyrins, Vol. III (ed. Dolphin, D.), p. 1, New York, Academic Press 1978

    Google Scholar 

  147. Kirner, J. F., Reed, C. A., Scheidt, W. R.: J. Am. Chem. Soc. 99, 1093 (1977)

    Google Scholar 

  148. Buchler, J. W., Habets, H., Van Kaam, J., Rohbock, K.: unpublished work

    Google Scholar 

  149. Cornillon, J. L., Anderson, J. E., Kadish, K. M.: Inorg. Chem. 25, 991 (1986)

    Google Scholar 

  150. Cornillon, J. L., Anderson, J. E., Kadish, K. M.: ibid. 25, 2611 (1986)

    Google Scholar 

  151. Ibers, J. A., Pace, L. J., Martinsen, J., Hoffman, B. M.: Struct. Bonding 50, 1 (1982)

    Google Scholar 

  152. Hanack, M., Pawlowski, G.: Naturwiss. 69, 266 (1982)

    Google Scholar 

  153. Hoffman, B. M., Ibers, J. A.: Acc. Chem. Res. 16, 15 (1983)

    Google Scholar 

  154. Onaka, S., Kondo, Y., Toriumi, K., Ito, T.: Chemistry Letters, 1605 (1980)

    Google Scholar 

  155. Barbe, J. M., Guilard, R., Lecomte, C., Gerardin, R.: Polyhedron 3, 889 (1984)

    Google Scholar 

  156. Onaka, S., Kondo, Y., Yamashita, M., Tatematsu, Y., Kato, Y., Goto, M., Ito, T.: Inorg. Chem. 24, 1070 (1985)

    Google Scholar 

  157. Kadish, K. M., Boisselier-Cocolios, B., Swistak, C., Barbe, J. M., Guilard, R.: ibid. 25, 121 (1986)

    Google Scholar 

  158. Collins, R. L., Petit, R.: J. Chem. Phys. 39, 3433 (1963)

    Google Scholar 

  159. Marks, T. J., Newman, A. R.: J. Am. Chem. Soc. 95, 769 (1973)

    Google Scholar 

  160. Cornwell, A. R., Harrison, P. G., Richards, J. A.: J. Organomet. Chem. 108, 47 (1976)

    Google Scholar 

  161. Burnham, R. A., Lyle, M. A., Stobart, S. R.: ibid. 125, 179 (1977)

    Google Scholar 

  162. Barbe, J. M.: Thèse de Troisième Cycle, p. 44, Dijon, France 1985

    Google Scholar 

  163. Cocolios, P., MoÏse, C., Guilard, R.: J. Organomet. Chem. 228, C43 (1982)

    Google Scholar 

  164. Guilard, R., Mitaine, P., MoÏse, C., Lecomte, C., Boukhris, A., Swistak, C., Tabard, A., Lacombe, D., Cornillon, J.-L., Kadish, K. M.: Inorg. Chem. in press (1987)

    Google Scholar 

  165. Martin, M., Rees, B., Mitschler, A.: Acta Cryst. B38, 6 (1982)

    Google Scholar 

  166. Zhu, N. J., Lecomte, C., Coppens, P., Keister, J. P.: ibid. B38, 1286 (1982)

    Google Scholar 

  167. Setsune, J., Yoshida, Z., Ogoshi, H.: J. Chem. Soc., Perkin I, 983 (1982)

    Google Scholar 

  168. Wayland, B. B., Newman, A.: Inorg. Chem. 20, 3093 (1981)

    Google Scholar 

  169. Collman, J. P., Barnes, C. E., Woo, L. K.: Proc. Natl. Acad. Sci. USA 80, 7684 (1983)

    Google Scholar 

  170. Collman, J. P., Barnes, C. E., Collins, T. J., Brothers, P. J.: J. Am. Chem. Soc. 103, 7030 (1981)

    Google Scholar 

  171. Collman, J. P., Barnes, C. E., Swepston, P. N., Ibers, J. A.: ibid. 106, 3500 (1984)

    Google Scholar 

  172. Collman, J. P., Woo, L. K.: Proc. Natl. Acad. Sci. USA 81, 2592 (1984)

    Google Scholar 

  173. Jones, N. L., Carroll, P. J., Wayland, B. B.: Organometallics 5, 33 (1986)

    Google Scholar 

  174. Cocolios, P., Chang, D., Vittori, O., Guilard, R., MoÏse, C., Kadish, K. M.: J. Am. Chem. Soc. 106, 572 (1984)

    Google Scholar 

  175. Guilard, R., Mitaine, P., Kadish, K. M.: manuscript in preparation

    Google Scholar 

  176. Guilard, R., Zrineh, A., Fechat, M., Tabard, A., Mitaine, P., Swistak, C., Kadish, K. M., submitted for publication

    Google Scholar 

  177. Kadish, K. M., Swistak, C., Boisselier-Cocolios, B., Barbe, J. M., Guilard, R.: Inorg. Chem., in press (1986)

    Google Scholar 

  178. Whitten, D. G., Yau, J. C., Carroll, F. A.: J. Am. Chem. Soc. 93, 2291 (1971)

    Google Scholar 

  179. Edwards, L., Dolphin, D., Gouterman, M., Adler, A. D.: J. Mol. Spect. 38, 16 (1971)

    Google Scholar 

  180. Landrum, J. T., Amini, M., Zuckerman, J. J.: Inorg. Chem. Acta 90, L73 (1984)

    Google Scholar 

  181. Fuhrhop, J. H., Kadish, K. M., Davis, D. G.: J. Am. Chem. Soc. 95, 5140 (1973)

    Google Scholar 

  182. Kadish, K. M.: Redox Reactions in Metalloporphyrins, in: Progress in Inorganic Chemistry (ed. Lippard, S.), Vol. 34, p. 435, New York, Academic Press 1986

    Google Scholar 

  183. Connelly, N. G., Geiger, W. E.: The Electron-Transfer Reactions of Mononuclear Organotransition Metal Complexes, in: Advances in Organometallic Chemistry (eds. Stone, F. G. A., West, R.), Vol. 23, p. 24, New York, Academic Press 1984

    Google Scholar 

  184. Baral, S., Hambright, P., Neta, P.: J. Phys. Chem. 88, 1595 (1984)

    Google Scholar 

  185. Cramer, S. P., Dawson, J. H., Hodgson, K. O., Hager, L. P.: J. Am. Chem. Soc. 100, 7282 (1980)

    Google Scholar 

  186. Dolphin, D., James, B. R., Welborn, H. C.: Enzymatic and Electrochemical Reduction of Dioxygen, in: Electrochemical and Spectroelectrochemical Studies of Biological Redox Components (ed. Kadish, K. M.), p. 563, Washington, American Chemical Soc. 1982

    Google Scholar 

  187. Dawson, J. H., Trudell, J. R., Barth, G., Linder, R. E., Bunnenburg, E., Djerassi, C., Chiang, R., Hager, L. P.: J. Am. Chem. Soc. 98, 3709 (1976)

    Google Scholar 

  188. English, D. R., Hendrickson, D. N., Suslick, K. S., Eigenbrot, C. W., Scheidt, W. R.: ibid. 106, 7258 (1984)

    Google Scholar 

  189. Gunter, M. J., Mander, L. N., McLaughlin, G. M., Murray, K. S., Berry, K. J., Clark, P. E., Buckingham, D. A.: ibid. 102, 1470 (1980)

    Google Scholar 

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Authors and Affiliations

  1. Faculté des Sciences “Gabriel”, Laboratoire de Synthèse et d'Electrosynthèse Organométallique associé au C.N.R.S. (UA 33), 6, Boulevard Gabriel, 21100, Dijon, France

    R. Guilard

  2. Faculté des Sciences, Centre de 2eme Cycle, Laboratoire de Minéralogie et Cristallographie (UA CNRS 809), Boite Postale nℴ 239, 54506, Vand∄uvre les Nancy Cedex, France

    C. Lecomte

  3. Department of Chemistry, University of Houston, 77004, Houston, Texas, USA

    K. M. Kadish

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  1. R. Guilard
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  2. C. Lecomte
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  3. K. M. Kadish
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Johann Walter Buchler

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Guilard, R., Lecomte, C., Kadish, K.M. (1987). Synthesis, electrochemistry, and structural properties of porphyrins with metal-carbon single bonds and metal-metal bonds. In: Buchler, J.W. (eds) Metal Complexes with Tetrapyrrole Ligands I. Structure and Bonding, vol 64. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0036792

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  • DOI: https://doi.org/10.1007/BFb0036792

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