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Nickel Catalysed Syntheses of Methyl-Substituted Cyclic Olefins, an Example of Stepwise Carbon-Carbon Bond Formation Promoted by a Transition Metal Complex

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Aspects of Homogeneous Catalysis

Part of the book series: Aspects of Homogeneous Catalysis ((AHCA,volume 2))

Abstract

The cyclotrimerization of buta-l,3-diene to cyclododeca-l,5,9-triene was discovered by G. Wilke in 1956 during an investigation concerned with the effect of titanium and chromium containing Ziegler catalysts on 1,3-diolefins. In the presence of a TiCl4/(C2H5)2AlCl-catalyst butadiene reacts forming predominantly trans, trans, cis-cyclododeca-l,5,9-triene, whereas on using a catalyst prepared from chromul chloride and aluminium triethyl a mixture of 60% all-trans- and 40% trans, trans, cis-cyclododeca-1,5,9-triene is obtained [1].

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References

  1. H. BREIL, P. HEIMBACH, M. KRÖNER, H. MÜLLER and G. WILKE, “Makromolekulare Chem.”, 69, 18, (1963).

    CAS  Google Scholar 

  2. H. W. B. REED, “J. Chem. Soc.”, 1931, (1954).

    Google Scholar 

  3. W. REPPE and W. J. SCHWECKENDIEK, “Annalen”, 560, 104, (1948).

    CAS  Google Scholar 

  4. G. WILKE et al., “Angew. Chem.” 75, 10 (1963).

    CAS  Google Scholar 

  5. G. WILKE et al., “Angew. Chem. Int. Ed.”, 2, 1, (1963).

    Google Scholar 

  6. G. WILKE, Paper presented at the Xth International Conference on Coordination Chemistry, Tokyo and Nikko, Japan (1967).

    Google Scholar 

  7. P. HEIMBACH, Mod. Chem. Ind., Pure and Applied Chemistry Symposium, Eastbourne, p. 223 (1968).

    Google Scholar 

  8. P. HEIMBACH, P. W. JOLLY and G. WILKE, “Adv. in Organometall. Chem.” 8, 29, (1970) Ed. F. G. A. Stone and R. West, Academic Press (New York).

    Google Scholar 

  9. G. P. CHIUSOLI, “Aspects Homogen. Cat.” 1, 11, (1970) Ed. R. Ugo, Manfredi (Milan).

    Google Scholar 

  10. B. BOGDANOVIČ, P. HEIMBACH, M. KRÖNER and G. WILKE, E. G. HOFFMANN and J. BRANDT, “Annalen”, 727, 143, (1969).

    Google Scholar 

  11. W. BRENNER, P. HEIMBACH, H. HEY, E. W. MÜLLER and G. WILKE, “Annalen”, 727, 161, (1969).

    CAS  Google Scholar 

  12. P. HEIMBACH and G. WILKE, “Annalen” 727, 183, (1969).

    CAS  Google Scholar 

  13. W. BRENNER, P. HEIMBACH and G. WILKE, “Annalen”, 727, 194, (1969).

    CAS  Google Scholar 

  14. W. BRENNER, P. HEIMBACH, K. J. PLONER and F. THÖMEL, “Angew. Chem.”, 81, 744, (1969)

    Google Scholar 

  15. W. BRENNER, P. HEIMBACH, K. J. PLONER and F. THÖMEL “Angew. Chem. Int. Ed.”, 8, 753, (1969).

    CAS  Google Scholar 

  16. P. HEIMBACH, “Chimia”, 23, 274, (1969).

    Google Scholar 

  17. A. C. COPE and E. M. HARDY, “J. Amer. Chem. Soc.”, 62, 441, (1940).

    CAS  Google Scholar 

  18. W. v. E. DOERING and W. R. ROTH, “Angew. Chem.”, 75, 27, (1963)

    CAS  Google Scholar 

  19. W. v. E. DOERING and W. R. ROTH, “Angew. Chem. Int. Ed.”, 2, 115, (1963).

    Google Scholar 

  20. E. VOGEL, “Annalen”, 615, 1, (1958).

    CAS  Google Scholar 

  21. H. HEY, Dissertation, Ruhr-Universität Bochum (1969).

    Google Scholar 

  22. G. S. HAMMOND and C. D. DE BOER, “J. Amer. Chem. Soc.”, 86, 899, (1964).

    CAS  Google Scholar 

  23. P. HEIMBACH and W. BRENNER, “Angew. Chem.”, 79, 814, (1967)

    Google Scholar 

  24. P. HEIMBACH and W. BRENNER, “Angew. Chem. Int. Ed.”, 6, 800, (1967).

    Google Scholar 

  25. P. HEIMBACH and H. HEY, “Angew. Chem.”, 82, 550, (1970)

    Google Scholar 

  26. P. HEIMBACH and H. HEY, “Angew. Chem. Int. Ed.”, 9, 528, (1970).

    CAS  Google Scholar 

  27. C. A. GROB, H. LINK and P. W. SCHIESS, “Helv. Chim. Acta”, 46, 483, (1963).

    CAS  Google Scholar 

  28. P. HEIMBACH, “Angew. Chem.”, 76, 859 (1964)

    CAS  Google Scholar 

  29. P. HEIMBACH, “Angew. Chem. Int. Ed.”, 3, 702, (1964).

    Google Scholar 

  30. H. BUCHHOLZ, Dissertation, Ruhr-Universität Bochum (1971).

    Google Scholar 

  31. N. BALCIOGLU, Dissertation, Ruhr-Universität Bochum (1970).

    Google Scholar 

  32. D. W. JOHNSON, Dissertation, University of Wisconsin (1970).

    Google Scholar 

  33. D. CRAIG, “J. Amer. Chem. Soc.”, 72, 1678 (1950)

    CAS  Google Scholar 

  34. D. CRAIG, “J. Amer. Chem. Soc.”, 83, 2885, (1961).

    CAS  Google Scholar 

  35. W. v. E. DOERING, R. G. BUTTERY, R. G. LAUGHLIN and N. CHAUDHURY, “J. Amer. Chem. Soc.”, 78, 3224, (1956).

    CAS  Google Scholar 

  36. C. SIMMONS, B. RICHARDSON and I. DVORETZKY, Gas Chromatography, p. 211, (1960) Butterworths (London).

    Google Scholar 

  37. T. DVORETZKY, D. B. RICHARDSON and C. R. DURETT, “Anal. Chem.”, 35, 545, (1963).

    CAS  Google Scholar 

  38. G. SCHOMBURG, in preparation.

    Google Scholar 

  39. G. SCHOMBURG “Anal. Chim. Acta”, 38, 45, (1967).

    CAS  Google Scholar 

  40. A. MATUKUMA, “J. Chem. Soc.”, 770, (1963).

    Google Scholar 

  41. A. MATUKUMA, Gas Chromatography, p. 55, (1968), The Institute of Petroleum (London).

    Google Scholar 

  42. G. SCHOMBURG, “J. CHROMATOG.”, 23, 18, (1966)

    CAS  Google Scholar 

  43. G. SCHOMBURG, “Adv. in Chromatography”, 6, 211, (1968).

    CAS  Google Scholar 

  44. K. R. KOPECKY, G. S. HAMMOND and P. A. LEERMAKERS, “J. Amer. Chem. Soc.”, 84, 1015, (1962).

    CAS  Google Scholar 

  45. G. SCHOMBURG, unpublished.

    Google Scholar 

  46. K. G. UNTCH and D. J. MARTIN, “J. Amer. Chem. Soc.”, 87, 3518, (1965).

    CAS  Google Scholar 

  47. H. BUCHHOLZ, P. HEIMBACH, G. SCHOMBURG and G. WILKE, in preparation.

    Google Scholar 

  48. E. KOVATS, “Helv. Chim. Acta”, 41, 1915, (1958)

    CAS  Google Scholar 

  49. E. KOVATS, “Anal. Chem.”, 36, 31 A, (1964).

    Google Scholar 

  50. H. SELBECK, Dissertation, Ruhr-Universität Bochum (1972).

    Google Scholar 

  51. P. HEIMBACH, G. SCHOMBURG, H. SELBECK and G. WILKE, unpublished.

    Google Scholar 

  52. D. HENNEBERG and G. SCHOMBURG, “Z. Analyt. Chem.”, 215, 424, (1965).

    CAS  Google Scholar 

  53. P. HEIMBACH, “Angew. Chem.”, 22, 967, (1968)

    Google Scholar 

  54. P. HEIMBACH, “Angew. Chem. Int. Ed.”, 7, 882, (1968).

    CAS  Google Scholar 

  55. W. FLECK, Dissertation, Ruhr-Universität Bochum (1971)

    Google Scholar 

  56. W. FLECK, P. HEIMBACH, D. HENNEBERG and G. SCHOMBURG, in preparation.

    Google Scholar 

  57. J. C. TREBELLAS, J. R. OLECHOWSKY and H. B. JONASSEN, “J. Organomet. Chem.”, 6, 412, (1966).

    CAS  Google Scholar 

  58. P. HEIMBACH, W. BRENNER, H. HEY and G. WILKE, Progress in Coordination Chemistry, Proceeding of the XI I.C.C.C., Haifa, Jerusalem, p. 10 (1968); Koordinationschemie der Übergangselemente Vortragsberichte Sektion C, Jena, p. 62, (1969).

    Google Scholar 

  59. P. HEIMBACH and H. HEY, “Annalen”, in preparation.

    Google Scholar 

  60. P. HEIMBACH, H. SELBECK and E. TROXLER, “Angew Chem.”, 83, 731 (1971)

    Google Scholar 

  61. P. HEIMBACH, H. SELBECK and E. TROXLER, “Angew. Chem. Int. Ed.”, 10, 659, (1971).

    CAS  Google Scholar 

  62. P. BINGER, H. BUCHHOLZ and P. HEIMBACH, in preparation.

    Google Scholar 

  63. H. J. KAMINSKY, Dissertation, Technische Hochschule Aachen (1962).

    Google Scholar 

  64. G. WILKE and H. MÜLLER, unpublished results.

    Google Scholar 

  65. P. HEIMBACH, paper presented at Leeds-Sheffield Symposium, Leeds (1971).

    Google Scholar 

  66. P. W. JOLLY, I. TKATCHENKO and G. WILKE, “Angew. Chem.”, 83, 328, (1971)

    Google Scholar 

  67. P. W. JOLLY, I. TKATCHENKO and G. WILKE, “Angew. Chem. Int. Ed.”, 10, (1971).

    Google Scholar 

  68. P. W. JOLLY, I. TKATCHENKO and G. WILKE, “Angew. Chem.”, 83, 329, (1971)

    Google Scholar 

  69. P. W. JOLLY, I. TKATCHENKO and G. WILKE, “Angew. Chem. Int. Ed.”, 10, (1971).

    Google Scholar 

  70. H. HEY, “Angew. Chem.”, 83, 144 (1971)

    Google Scholar 

  71. H. HEY, “Angew. Chem. Int. Ed.”, 10, (1971).

    Google Scholar 

  72. F. A. COTTON, “J. Amer. Chem. Soc.”, 90, 6230, (1968).

    CAS  Google Scholar 

  73. P. HEIMBACH and H. LEHMKUHL, in preparation.

    Google Scholar 

  74. C. A. TOLMAN, “J. Amer. Chem. Soc.”, 92, 2953, (1970).

    CAS  Google Scholar 

  75. C. A. TOLMAN, “J. Amer. Chem. Soc.”, 92, 2956, (1970).

    CAS  Google Scholar 

  76. H. BÖNNEMANN, unpublished results.

    Google Scholar 

  77. P. HEIMBACH, paper presented at Leeds-Sheffield Symposium, Sheffield (1969) and Inorganic Symposium, Canberra (1969).

    Google Scholar 

  78. R. HUISGEN, “Angew. Chem.”, 19, 783, (1970)

    Google Scholar 

  79. R. HUISGEN, “Angew. Chem. Int. Ed.”, 9, 314, (1970).

    Google Scholar 

  80. F. THÖMEL, Dissertation, Ruhr-Universität Bochum (1970).

    Google Scholar 

  81. P. HEIMBACH, K. J. PLONER and F. THÖMEL, “Angew. Chem.”, 83, 285, (1971)

    Google Scholar 

  82. P. HEIMBACH, K. J. PLONER and F. THÖMEL, “ANGEW. CHEM. INT. ED.”, 10, (1971).

    Google Scholar 

  83. W. RING, Chemische Werke Hüls, Offenlegungsschrift, DAS 1902, 274, (1970).

    Google Scholar 

  84. P. HEIMBACH, W. RING, F. THÖMEL, and W. ZADV unpublished.

    Google Scholar 

  85. W. REPPE, N. V. KUTEPOW and A. MAGIN, “Angew. Chem.”, 81, 717, (1969)

    Google Scholar 

  86. W. REPPE, N. V. KUTEPOW and A. MAGIN, “Angew. Chem. Int. Ed.”, 8, 727, (1969).

    CAS  Google Scholar 

  87. P. HEIMBACH, unpublished results.

    Google Scholar 

  88. KOERNER von GUSTORF, personal communication.

    Google Scholar 

  89. H. BÖNNEMANN, paper presented at Leeds-Sheffield Symposium, Sheffield (1969).

    Google Scholar 

  90. B. BOGDANOVIČ and G. WILKE, “Brennstoffchemie”, 49, 323, (1968).

    Google Scholar 

  91. B. BOGDANOVIČ, B. HENC, H. G. KARMANN, H. G. NÜSSEL, D. WALTER and G. WILKE, “Industrial and Engineering Chemistry”, 62, 34, (1970).

    Google Scholar 

  92. H. BÖNNEMANN, H. SCHENKLUHN and G. WILKE, unpublished results; H. BÖNNEMANN, paper presented at Leeds-Sheffield Symposium, Leeds (1971).

    Google Scholar 

  93. H. SCHENKLUHN, Dissertation, Ruhr-Universität Bochum (1971).

    Google Scholar 

  94. G. HERRMANN and G. WILKE, “Angew. Chem.”, 74, 693, (1962)

    Google Scholar 

  95. G. HERRMANN and G. WILKE, “Angew. Chem. Int. Ed.”, 1, 549, (1962).

    Google Scholar 

  96. K. JONAS, Dissertation, Ruhr-Universität Bochum (1968).

    Google Scholar 

  97. G. WILKE and K. JONAS, unpublished results.

    Google Scholar 

  98. C. DELLIEHAUSEN, Dissertation, Ruhr-Universität Bochum (1968).

    Google Scholar 

  99. P. HEIMBACH and G. WILKE, unpublished results.

    Google Scholar 

  100. P. HEIMBACH and R. TRAUNMÜLLER, Chemie der Metall-Olefin Komplexe, (1970), Verlag Chemie (Weinheim).

    Google Scholar 

  101. K. J. PLONER, Dissertation, Ruhr-Universität Bochum (1969).

    Google Scholar 

  102. J. HALPERN, “Acc. Chem. Res.”, 3, 386, (1970).

    CAS  Google Scholar 

  103. J. P. COLLMAN, “Acc. Chem. Res.”, 1, 136, (1968).

    CAS  Google Scholar 

  104. L. VASKA and J.W. DILUZIO, “J. Amer. Chem. Soc.”, 83, 2784, (1961).

    CAS  Google Scholar 

  105. L. Vaska, “Acc. Chem. Res.”, 1, 186, (1968).

    Google Scholar 

  106. K. JONAS and G. WILKE, “Angew. Chem.”, 81, 534, (1969)

    Google Scholar 

  107. K. JONAS and G. WILKE, “Angew. Chem. Int. Ed.”, 1, 519, (1969).

    Google Scholar 

  108. G. WILKE and K. JONAS, unpublished results.

    Google Scholar 

  109. T. H. COFFIELD, J. KOZIKOWSKI AND R. N. CLOSSON, “J. Org. Chem.”, 22, 598, (1957).

    CAS  Google Scholar 

  110. K. A. KEBLYS and A. H. FILBEY, “J. Amer. Chem. Soc.”, 82, 4204, (1960).

    CAS  Google Scholar 

  111. F. CALDERAZZO, “Inorg. Chem.”, 4, 293, (1965).

    CAS  Google Scholar 

  112. R. J. MAWBY, F. BASOLO and R. G. PEARSON, “J. Amer. Chem. Soc.”, 86, 3994, (1964).

    CAS  Google Scholar 

  113. F. CALDERAZZO and F. A. COTTON, “Chimica e Industria” (Milan), 46, 1165, (1964).

    CAS  Google Scholar 

  114. G. LEFÉBVRE and Y. CHAUVIN, “Aspects Homog. Catalysis”, 1, 108, (1970). Ed. R. Ugo, Manfredi (Milan).

    Google Scholar 

  115. G. HENRICI-OLIVÉ and S. OLIVé, Polymerisation (Katalyse, Kinetik, Mechanism), 1970 Verlag Chemie (Weinheim).

    Google Scholar 

  116. R. B. Woodward and R. Hoffmann, “Angew. Chem.”, 81, 797, (1969)

    Google Scholar 

  117. R. B. Woodward and R. Hoffmann, “Angew. Chem. Int. Ed.”, 8, 781, (1969).

    CAS  Google Scholar 

  118. F. D. MANGO and J. H. SCHACHTSCHNEIDER, “J. Amer. Chem. Soc.”, 89, 2484, (1967).

    CAS  Google Scholar 

  119. F. D. MANGO and J. H. SCHACHTSCHNEIDER, “J. Amer. Chem. Soc.”, 91, 1030, (1969).

    CAS  Google Scholar 

  120. F. D. MANGO and J. H. SCHACHTSCHNEIDER, “J. Amer. Chem. Soc.”, 93, 1123, (1971).

    CAS  Google Scholar 

  121. F. D. MANGO, “Adv. in Catalysis”, 20, 291, (1970).

    Google Scholar 

  122. R. PETTIT, H. SUGAHARA, J. WRISTERS and W. MERK, “Disc. Far Soc.”, 47, 71, (1969).

    Google Scholar 

  123. G. S. LEWANDOS and R. PETTIT, “Tetrahedron Lett.”, 789, (1971).

    Google Scholar 

  124. F. D. MANGO, “Tetrahedron Lett.”, 6, 505, (1971).

    Google Scholar 

  125. L. CASSAR, P. E. EATON and J. HALPERN, “J. Amer. Chem. Soc.”, 92, 515, (1970).

    Google Scholar 

  126. TH. J. KATZ, N. ACTON and S. CEREFICE, “J. Amer. Chem. Soc.”, 91, 206 and 2405, (1969).

    CAS  Google Scholar 

  127. W. TH. A. M. VAN DERLUGT, “Tetrahedron Lett.”, 2281, (1970).

    Google Scholar 

  128. R. TRAUNMÜLLER, Dissertation, Universität Wien (1969).

    Google Scholar 

  129. R. TRAUNMüLLER, O. E. POLANSKY, P. HEIMBACH and G. WILKE, “Chemical Physics Letters”, 3, 300, (1969).

    Google Scholar 

  130. R. HUISGEN, A. DAHMEN and H. HUBER, “J. Amer. Chem. Soc.”, 89, 7130, (1967).

    CAS  Google Scholar 

  131. C. P. C. BRADSHAW, E. J. HOWMANN and L. TURNER, “J. Catalysis”, 7, 269, (1967).

    CAS  Google Scholar 

  132. E. A. ZUECH, “Chem. Comm.”, 1182, (1968).

    Google Scholar 

  133. C. T. ADAMS and S. G. BRANDENBERGER, “J. Catalysis”, 13, 360, (1969).

    CAS  Google Scholar 

  134. N. CALDERÓN, H. Y. CHEN and K. W. SCOTT, “Tetrahedron Lett.”, 3327, (1967).

    Google Scholar 

  135. C.A. TOLMAN, Chem. Soc. Reviewes in press.

    Google Scholar 

  136. BÖNNEMANN, Ch. GYRARD, W. KOPP and G. WILKE, Special Lectures XXIII. Internat. Congr. Pune Applied Chem., Boston, 6, 265, (1971) Butterworths.

    Google Scholar 

  137. LEWIS and R. S. NYHOLM, Special Lectures XXIII. Internat. Congr. Pure Applied Chem. Boston 6, 61, (1971) Butterworths.

    Google Scholar 

  138. L. CASSAR, P. E. EATON and J. HALPERN, “J. Amer. Chem. Soc.” 92, 3515, (1970).

    CAS  Google Scholar 

  139. H. BUCHHOLZ, P. HEIMBACH, H. HEY, H. SELBECK and W. WIESE, “Coord. Chem. Rev., in press.

    Google Scholar 

  140. J. P. COLLMAN, P. EAMHANN and G. DOLCETTI, “J. Amer. Chem. Soc.”, 93, 1788, (1971).

    CAS  Google Scholar 

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  1. Max-Planck-Institut für Kohlenforschung Mülheim, Ruhr, Germany

    P. Heimbach

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  1. Istituto Di Chimica Generale Ed Inorganica, Milan University, Italy

    Renato Ugo

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Heimbach, P. (1974). Nickel Catalysed Syntheses of Methyl-Substituted Cyclic Olefins, an Example of Stepwise Carbon-Carbon Bond Formation Promoted by a Transition Metal Complex. In: Ugo, R. (eds) Aspects of Homogeneous Catalysis. Aspects of Homogeneous Catalysis, vol 2. Springer, Dordrecht. https://doi.org/10.1007/978-94-010-2285-9_3

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