Polymer-Bound Phosphine Catalysts

  • Norman L. Holy
Part of the Modern Inorganic Chemistry book series

Abstract

While the theme of this volume is catalysis in a single phase, the principles and dynamics of homogeneous catalysis have impacted other areas of catalysis as well. Today, more than ever, there is an overlapping, a meshing of concepts from homogeneous and heterogeneous catalysis. One of the areas that interfaces both classical divisions is catalysis via polymer-bound transition metal complexes. It is an interface area because catalysts are prepared typically from an organic polymer such as polystyrene and then, after attachment of a ligand, a soluble metal complex is bound. The choice of metal complex is almost always based upon examples from homogeneous catalysis. One of the principal motivations for attaching a soluble complex to a polymer is that catalyst recovery becomes much easier. There are, however, motivations beyond simple recovery considerations for examining the reactions of polymer-bound catalysts. Though the characteristics of the polymer-bound phosphines may be described to a first approximation as being predictable on the basis of the properties, performances, and mechanistic interpretations of the homogeneous analogs, the support often has a significant influence on catalytic activity. For example, a polymerbound catalyst may give a product distribution quite different from that of the soluble catalyst. Moreover, it is often observed that polymer-supported catalysts are less oxygen sensitive than the homogeneous ones.

Keywords

Catalysis Oligomerization Ketone Ruthenium Siloxane 

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References

  1. 1.
    C. U. Pittman, Polymer-Supported Reactions in Organic Synthesis, edited by P. Hodge and D. C. Sherrington ( John Wiley and Sons, New York, 1980 ), p. 249.Google Scholar
  2. 2.
    Y. Chauvin, D. Commereuc, and F. Dawans, Prog. Polym. Sci. 5, 95 - 226 (1977).CrossRefGoogle Scholar
  3. 3.
    a. E. Bayer and V. Schurig. Chem. Technol. 1976, 212. b. E. Bayer and V. Schurig, Angew. Chem. Inti. Edn. 14, 493 - 494 (1975).Google Scholar
  4. 4.
    G. Bernard, Y. Chauvin, and D. Commereuc, Bull. Soc. Chim. 1163, 1168 - 72 (1976).Google Scholar
  5. 5.
    W. Heitz, Adv. Pdym. Sci. 23, 1 (1977).CrossRefGoogle Scholar
  6. 6.
    M. J. Farrall and J. M. Frechet, J. Org. Chem. 43, 2618 (1978).CrossRefGoogle Scholar
  7. 7.
    K. A. Abdula, N. P. Allen, A. H. Badran, J. Dwyer, C. A. McAuliffe, and N. D. A. Toma, Chem. Ind. 273 (1976).Google Scholar
  8. 8.
    R. D. Sanner, R. G. Austin, M. S. Wrighton, W. D. Honnick, and C. U. Pittman, Jr., “Interfacial Photoprocesses: Energy Conversion and Synthesis,” ACS Adv. in Chem. Sere 184, 1980, 13; C. U. Pittman, Jr., W. D. Honnick, M. S. Wrighton, R. D. Sanner, R. G. Austin, Fundamental Research in Homogeneous Catalysis, edited by M. Tsutsui (Plenum Publishing, 1979 ), p. 603.Google Scholar
  9. 9.
    R. H. Grubbs and L. C. Kroll, J. Am. Chem. Soc. 93, 3062 (1971).CrossRefGoogle Scholar
  10. 10.
    H. S. Bruner and J. C. Bailar, Inorg. Chem. 12, 1465 (1973).CrossRefGoogle Scholar
  11. 11.
    R. Pierantozzi, K. J. McQuade, B. C. Gates, M. Wolf, H. Knozinger, and W. Ruhmann, J. Am. Chem. Soc. 101, 5436 (1979).CrossRefGoogle Scholar
  12. 12.
    C. U. Pittman, Jr., L. R. Smith, and R. M. Hanes, J. Am. Chem. Soc. 97, 1742 (1975).Google Scholar
  13. 13.
    G. O. Evans, C. U. Pittman, Jr., R. McMillan, R. T. Beach, and R. Jones, J. Organometal. Chem. 67, 295 (1974).Google Scholar
  14. 14.
    C. U. Pittman, Jr. and L. R. Smith, J. Am. Chem. Soc. 97, 1749 (1975).Google Scholar
  15. 15.
    R. H. Grubbs, S. Swetnick, and S. C. H. Su, J. Mol. Catal. 3, 11-15 (1977-1978).Google Scholar
  16. 16.
    M. Capka, P. Svoboda, M. Kraus, and J. Hetflejs, Chem. Ind., 650 - 651 (1972).Google Scholar
  17. 17.
    T. H. Kim and H. F. Rase, Ind. Eng. Chem. Prod. Res. Dev. 15, 249 - 254 (1976).CrossRefGoogle Scholar
  18. 18.
    M. Czakova and M. Capka, J. Mol. Catal. 11, 313 - 322 (1981).CrossRefGoogle Scholar
  19. 19.
    K. G. Allum, R. D. Hancock, S. McKenzie, and R. C. Pitkethly, Proceedings of the Fifth International Congress on Catalysis 1972, edited by J. W. Hightower (North Holland, Amsterdam, 1973), Vol. 1, p. 447.Google Scholar
  20. 20.
    R. D. Hancock, I. V. Howell, R. C. Pitkethly, and P. J. Robinson, Catalysis Heterogeneous and Homogeneous, edited by B. Delmon and G. Jannes ( Elsevier, Amsterdam, 1975 ), pp. 349 - 359.Google Scholar
  21. 21.
    K. G. Allum, R. D. Hancock, I. V. Howell, R. C. Pitkethly, and P. T. Robinson, J. Catalysis 43, 322 - 330 (1976).CrossRefGoogle Scholar
  22. 22.
    K. G. Allum, R. D. Hancock, I. V. Howell, T. E. Lester, S. McKenzie, R. C. Pitkethly, and P. J. Robinson, J. Catalysis 43, 331 (1976).CrossRefGoogle Scholar
  23. 23.
    K. G. Allum, R. D. Hancock, I. V. Howell, T. E. Lester, S. McKenzie, R. C. Pitkethly, and P. J. Robinson, J. Organometallic Chem. 107, 393 (1976).CrossRefGoogle Scholar
  24. 24.
    K. G. Allum, R. D. Hancock, I. V. Howell, S. McKenzie, R. C. Pitkethly, and P. J. Robinson, J. Organomet. Chem. 87, 203 (1975).CrossRefGoogle Scholar
  25. 25.
    J. M. Moreto, J. Albaiges, and F. Camps, Catalysis Heterogeneous and Homogeneous, edited by B. Delmon and G. Jannes ( Elsevier, Amsterdam, 1975 ), pp. 339 - 347.Google Scholar
  26. 26.
    K. Kochloefl, W. Liebelt, and H. Knozinger, J. Chem. Soc., Chem. Comm. 1977, 510.Google Scholar
  27. 27.
    M. Capka and J. Hetflejs, Coll. Czech. Chem. Comm. 39, 154 (1974).CrossRefGoogle Scholar
  28. 28.
    Badische Anilir und Soda-Fabrik, A. G., French Patent No.2 053 300.Google Scholar
  29. 29.
    K. G. Allum, R. D. Hancock, British Patent No.1 287 566.Google Scholar
  30. 30.
    J. Manassen, Israel J. Chem. 8, 5p (1970).Google Scholar
  31. 31.
    S. V. McKinley and J. W. Rakshys, United States Patent No.3 708462 (to Dow Chemical Company).Google Scholar
  32. 32.
    Y. Nonaka, S. Takahashi, and N. Hagihara, Mem. Inst. Sci. Ind. Res., Osaka Univ. 31, 23 (1974).Google Scholar
  33. 33.
    A. J. Naaktgeboren, R. J. M. Nolte, and W. Drenth, Reel. Trav. Chim. Pays-Bas 97, 112-(1978).Google Scholar
  34. 34.
    A. J. Naaktgeboren, R. J. M. Nolte, and W. Drenth, J. Amer. Chem. Soc. 102, 3350 (1980).CrossRefGoogle Scholar
  35. 35.
    J. Kiji, S. Kadoi, and J. Furukawa, Angew. Makromol. Chem. 46, 163 (1975).CrossRefGoogle Scholar
  36. 36.
    N. Takaishi, H. Imai, C. A. Bertelo, and J. K. Stille, J. Am. Chem. Soc. 98, 5400 (1976).CrossRefGoogle Scholar
  37. 37.
    N. Takaishi, H. Imai, C. A. Bertelo, and J. K. Stille, J. Am. Chem. Soc. 100, 264 (1978).CrossRefGoogle Scholar
  38. 38.
    G. L. Baker, S. J. Fritschel, and J. K. Stille, J. Org. Chem. 46, 2960 - 2965 (1981).CrossRefGoogle Scholar
  39. 39.
    I. Dietzmann, D. Tomanova, and J. Hetflejs, Coll. Czech. Chem. Comm. 39, 135 (1974).Google Scholar
  40. 40.
    C. U. Pittman, Jr. and L. R. Smith, J. Amer. Chem. Soc. 97, 341 (1975).Google Scholar
  41. 41.
    C. U. Pittman, Jr. and R. F. Felis, J. Organometallic Chem. 72, 399 (1974).Google Scholar
  42. 42.
    C. U. Pittman, Jr. and R. M. Hanes, J. Amer. Chem. Soc. 98, 5402 (1976).Google Scholar
  43. 43.
    K. G. Allum, R. D. Hancock, I. V. Howell, R. C. Pitkethly, and P. J. Robinson, J. Organometallic Chem. 87, 189 (1975).CrossRefGoogle Scholar
  44. 44.
    M. S. Jarrell and B. C. Gates, J. Catalysis 40, 255 (1975).CrossRefGoogle Scholar
  45. 45.
    D. Doskocilova, B. Schneider, and J. Jakes, J. Magn. Reson. 29, 79 (1978).Google Scholar
  46. 46.
    S. J. Fritschel, J. J. H. Ackerman, T. Keyser, and J. K. Stille, J. Org. Chem. 44, 3152 (1979).CrossRefGoogle Scholar
  47. 47.
    T. Imanaka, K. Kaneda, S. Teranishi, and M. Terasawa, Proceedings of the Sixth International Congress on Catalysis, 1976, edited by G. C. Bond, P. B. Wells, and F. C. Tompkins (The Chemical Society, London, 1977), Vol. 1, p. 509.Google Scholar
  48. 48.
    N. Takahashi, I. Okura, and T. Keii, J. Amer. Chem. Soc. 97, 7489 (1975).CrossRefGoogle Scholar
  49. 49.
    K. Kaneda, M. Terasawa, T. Imamaka, and S. Teranishi, Chem. Lett. 1005 - 1008 (1975).Google Scholar
  50. 50.
    N. L. Holy, Fundamental Research in Homogeneous Catalysis 3, edited by M. Tsutsui (Plenum Publishing, 1979 ), pp. 691 - 706.Google Scholar
  51. 51.
    J. Reed, P. Eisenberger, B.-K. Teo, and B. M. Kincaid, J. Amer. Chem. Soc. 99, 5217-5218 (1977); 100, 2375 - 2378 (1978).Google Scholar
  52. 52.
    L. D. Rollmann, J. Amer. Chem. Soc. 97, 2132 (1975).CrossRefGoogle Scholar
  53. 53.
    F. Pinna, M. Bonivento, G. Strukul, M. Graziani, E. Cernia, and N. Palladino, J. Mol. Catalysis 1, 309 (1975-1976).Google Scholar
  54. 54.
    G. Strukul, M. Bonivento, M. Graziani, E. Cernia, and N. Palladino, Inorge Chim. Acta 12, 15 (1975).CrossRefGoogle Scholar
  55. 55.
    M. Graziani, G. Strukul, M. Bonivento, F. Pinna, E. Cernia, and N. Pallidino, Catalysis Heterogeneousand Homogeneous, edited by B. Delmon and G. Jannes ( Elsevier, Amsterdam, 1975 ), pp. 331 - 338.Google Scholar
  56. 56.
    G. Strukul, P. Dolimpio, M. Bonivento, F. Pinna and M. Graziani, J. Mol. Catalysis 2, 179 (1977).CrossRefGoogle Scholar
  57. 57.
    D. Tatarsky, D. H. Kohn, and M. Cais, J. Polym. Sci., Polym. Chem. Ed. 18, 1387-1397 (1980).Google Scholar
  58. 58.
    R. H. Grubbs and E. M. Sweet, Macromolecules 8, 241 - 242 (1975).CrossRefGoogle Scholar
  59. 59.
    R. H. Grubbs, C. Gibbons, L. C. Kroll, W. D. Bonds, and C. H. Brubaker, Jr., J. Amer. Chem. Soc. 95, 2373 (1973).Google Scholar
  60. 60.
    J. Manassen, Reference 20, 293 - 306.Google Scholar
  61. 61.
    M. S. Bruner and J. C. Bailor, J. Amer. Oil Chem. Soc. 49, 533 (1972).CrossRefGoogle Scholar
  62. 62.
    R. H. Grubbs, L. C. Kroll, and E. M. Sweet, J. Macromol. Sci., Chem. A 7, 1047 (1973).CrossRefGoogle Scholar
  63. 63.
    J. D. Morrison, W. F. Masler, and M. F. Neuberg, Adv. Catal. 25, 81 (1976).CrossRefGoogle Scholar
  64. 64.
    B. D. Vineyard, W. S. Knowles, M. J. Sabacky, G. L. Bachman, and D. J. Weinkauff, J. Am. Chem. Soc. 99, 5946 - 5952 (1977).CrossRefGoogle Scholar
  65. 65.
    T. Masada and J. K. Stille, J. Am. Chem. Soc. 100, 268 (1978).CrossRefGoogle Scholar
  66. 66.
    G. C. Baker, S. J. Fritschel, J. R. Stille, and J. K. Stille, J. Org. Chem. 46, 2954 - 2960 (1981).CrossRefGoogle Scholar
  67. 67.
    W. Dumont, J. C. Poulin, T. P. Dang, and H. B. Kagan, J. Am. Chem. Soc. 95, 8295 - 8299 (1973).CrossRefGoogle Scholar
  68. 68.
    K. Achiwa, Chem. Lett. 905 (1978).Google Scholar
  69. 69.
    M. E. Wilson and G. M. Whitesides, J. Am. Chem. Soc. 100, 306 (1977).CrossRefGoogle Scholar
  70. 70.
    F. Ciardelli, E. Chiellini, C. Carlini, and R. Nocci, Polym. Preprints 17, 188 (1976).Google Scholar
  71. 71.
    a. K. Ohkubo, K. Fujimori, and K. Yoshinaga, norge Nucl. Chem. Lett. 15, 231-234 (1979). b. K. Ohkubo, M. Setoguchi, and K. Yoshinaga, norge Nucl. Chem. Lett. 15, 235 - 238 (1979).Google Scholar
  72. 72.
    C. U. Pittman, Jr., A. Hirao, J. J. Yang, Q. Ng, R. Hanes, and C. C. Lin, PreprintsDiv. Petrol. Chem. (ACS) 22, 1196 (1977).Google Scholar
  73. 73.
    C. F. Hobbs and W. S. Knowles, J. Org. Chem. 46, 4422 - 4427 (1981).CrossRefGoogle Scholar
  74. 74.
    J. I. Crowley and H. Rapoport, Ace. Chem. Res. 9, 135 - 144 (1976).CrossRefGoogle Scholar
  75. 75.
    L. T. Scott, J. Rebek, L. Oysyanko, and C. L. Sims, J. Am. Chem. Soc. 99, 625 - 626 (1977).CrossRefGoogle Scholar
  76. 76.
    P. Jayalekshmy and S. Mazur, J. Am. Chem. Soc. 98, 6710 - 6711 (1976).CrossRefGoogle Scholar
  77. 77.
    C. U. Pittman, Jr. and Q. Ng, J. Organometal. Chem. 153, 85 (1978).Google Scholar
  78. 78.
    R. H. Crabtree, M. F. Mellea, J. M. Mihelcic, and J. M. Quirk, J. Am. Chem. Soc. 104, 107 - 113 (1982).CrossRefGoogle Scholar
  79. 79.
    A. H. Janowicz and R. G. Bergman, J. Am. Chem. Soc. 104, 352 (1982).CrossRefGoogle Scholar
  80. 80.
    S. Jacobson, W. Clements, H. Hiramoto, and C. U. Pittman, Jr., J. Mol. Catal. 1, 73 (1975).CrossRefGoogle Scholar
  81. 81.
    C. U. Pittman, Jr., S. E. Jacobson, and H. Hiramoto, J. Am. Chem. Soc. 97, 4774 (1975).Google Scholar
  82. 82.
    B. C. Gates and J. Lieto, Chem. Technol. 248 (1980).Google Scholar
  83. 83.
    J. Andrieux, D. H. R. Barton, and H. Patin, J. Chem. Soc. Perkin I, 359 - 000 (1977).Google Scholar
  84. 84.
    C. A. Tolman, J. Am. Chem. Soc. 94, 2994 - 2999 (1972).CrossRefGoogle Scholar
  85. 85.
    R. G. Miller, P. A. Pinke, R. D. Stauffer, H. J. Golden, and D. J. Baker, J. Am. Chem. Soc. 96, 4211-4220 (1974); P. A. Pinke and R. G. Miller, op. cit., 4221-4229; P. A. Pinke, R. D. Stauffer, and R. G. Miller, op. cit. 4229 - 4234.Google Scholar
  86. 86.
    J. M. Moreto, J. Albaiges, and F. Camps, Ref. 20, 339 - 348.Google Scholar
  87. 87.
    P. A. Gosselain, Reference 20, 107 - 132.Google Scholar
  88. 88.
    J. Conan, M. Bartholin, and A. Guyot, J. Mol. Catalysis 1,375 (1975-1976).Google Scholar
  89. 89.
    K. Kochloefl, W. Liebelt, and H. Krozinger, J.C.S. Chem. Commun. 510 (1977).Google Scholar
  90. 90.
    I. V. Howell and R. D. Hancock, British Patent No.1 408 013.Google Scholar
  91. 91.
    W. R. Cullen, D. J. Patmore, A. J. Chapman, and A. D. Jenkins, J. Organometal. Chem. 102, C12 (1975).CrossRefGoogle Scholar
  92. 92.
    R. R. Schrock and J. Osborn, J.C.S., Chem. Commun. 567 (1970).Google Scholar
  93. 93.
    G. Pez, R. A. Grey, and J. Corsi, J. Am. Chem. Soc. 103, 7528 (1981).CrossRefGoogle Scholar
  94. 94.
    S. E. Jacobson and C. U. Pittman, Jr., J. Chem. Soc. Chem. Comm. 187 (1975).Google Scholar
  95. 95.
    M. H. J. M. DeCroon and J. W. E. Coenen, J. Mol. Catal. 11, 301 - 311 (1981).CrossRefGoogle Scholar
  96. 96.
    S. Lecolier, French Patent No.2 270 238.Google Scholar
  97. 97.
    M. Terasawa, K. Kaneda, T. Imanaka, and S. Teranishi, J. Catal. 51, 406 (1978).CrossRefGoogle Scholar
  98. 98.
    K. Kaneda, M. Terasawa, T. Imanaka, and S. Teranishi, Chem. Lett. Japan 995 (1976).Google Scholar
  99. 99.
    R. H. Grubbs, L. C. Kroll, and E. M. Sweet, Polymer Preprints 13, 828 (1972).Google Scholar
  100. 100.
    R. H. Grubbs, E. M. Sweet, and S. Phisanbut, Catalysis In Organic Synthesis, edited by P. Rylander and H. Greenfield ( Academic Press, New York, 1975 ), p. 153.Google Scholar
  101. 101.
    A. Guyot, C. Graillat, and M. Bartholin, J. Mol. Catal. 3, 39 (1977-1978).Google Scholar
  102. 102.
    K. G. Allum, R. D. Hancock, and R. C. Pitkethly, British Patent No.1 295 675.Google Scholar
  103. 103.
    C. U. Pittman, Jr. and G. Wilemon, Ann. N. Y. Acad. Sci. 333, 67 (1980).Google Scholar
  104. 104.
    J. P. Collman, L. S. Hegedus, M. P. Cooke, J. R. Norton, G. Golcetti, and D. N. Marquart, J. Am. Chem. Soc. 94, 1789 (1972).CrossRefGoogle Scholar
  105. 105.
    M. S. Jarrell, B. C. Gates, and E. D. Nicholson, J. Am. Chem. Soc. 100, 5727 (1978).CrossRefGoogle Scholar
  106. 106.
    M. S. Jarrel and B. C. Gates, J. Catal. 54, 81 (1978).CrossRefGoogle Scholar
  107. 107.
    Z. Otero-Schipper, Z. Lieto, and B. C. Gates, J. Catal. 63, 175 (1980).CrossRefGoogle Scholar
  108. 108.
    J. Lieto, J. J. Rafalko, and B. C. Gates, J. Catal. 62, 149 (1980).CrossRefGoogle Scholar
  109. 109.
    J. J. Rafalko, J. Lieto, B. C. Gates, and G. L. Schrader, Jr., J. Chem. Soc., Chem. Commun. 540 (1978).Google Scholar
  110. 110.
    C. U. Pittman, Jr., S. K. Wuu, and S. E. Jacobson, J. Catal. 44, 87 (1976).Google Scholar
  111. 111.
    C. U. Pittman: Heterogeneous and Homogeneous, edited by B. Delman and G. Jannes ( Elsevier, Amsterdam, 1975 ), p. 393.Google Scholar
  112. 112.
    A. J. Naaktgeboren, R. J. M. Notte, and W. Drenth, J. Mol. Catal. 11, 343 - 351 (1981).CrossRefGoogle Scholar
  113. 113.
    R. G. Muratova, R. Z. Khairullina, S. V. Shulyndin, B. E. Ivanov, and R. I. Izmailov, Kin. and Catal. 15, 115 (1974).Google Scholar
  114. 114.
    G. L. Baker, S. J. Fritschel, and J. K. Stille, Polymer Preprints 22 (1), 155 (1981).Google Scholar
  115. 115.
    W. R. Cullen, D. J. Patmore, A. J. Champan, and A. D. Jenkins, J. Organomet. Chem. 102, C12 (1975).CrossRefGoogle Scholar
  116. 116.
    B. Bogdanovic, H. Biserka, H. G. Karmann, H. G. Nussel, D. Walter, and G. Wilke, Ind. Eng. Chem. 62, 34 - 38 (1970).CrossRefGoogle Scholar
  117. 117.
    R. S. Bauer, H. Chung, P. W. Glockner, and W. Keim, United States Patent No. 3 644563 (1972); R. F. Mason, United States Patent No. 3 737475 (1973).Google Scholar
  118. 118.
    Badische Anilin und Soda Fabrik A.G., French Patent No.2 053 300.Google Scholar
  119. 119.
    K. Kaneda, M. Terasawa, T. Imanaka, and S. Teranishi, Tetrahedron Lett. 2957 (1977).Google Scholar
  120. 120.
    K. Kaneda, T. Uchiyama, M. Terasawa, T. Imanaka, and S. Teranishi, Chem. Lett. Japan 449 (1976).Google Scholar
  121. 121.
    C. U. Pittman, Jr. and S. E. Jacobson, J. Mol. Catal. 3,293-297 (1977-1978).Google Scholar
  122. 122.
    F. Hobjabri, Polymer 17, 58 (1976).CrossRefGoogle Scholar
  123. 123.
    H. Pracejus, German Patent No.2 230739.Google Scholar
  124. 124.
    K. G. Allum and R. D. Hancock, Fifth International Congress of Catalysis, Preprint31 (Miami, 1972 ).Google Scholar
  125. 125.
    R. F. Clark, C. D. Storrs, and G. B. Barnes, United States Patent No.3 364273.Google Scholar
  126. 126.
    J. L. Speier, “Homogeneous Catalysis by Transition Metals,” Adv. Organomet. Chem. 17, 407 (1979).CrossRefGoogle Scholar
  127. 127.
    I. Dietzmann, D. Tomanova, and J. Hetflejs, Coll. Czechoslov. Chem. Comm. 39, 123 (1974).CrossRefGoogle Scholar
  128. 128.
    V. D. Luedeke, A dipronitrile, edited by J. J. McKetta and W. A. Cunningham, Encyclopedia of Chemical Processing and Design (Marcel Dekker, 1977 ), Vol. 2, p. 146.Google Scholar
  129. 129.
    M. Capka, P. Svoboda, M. Corny, and J. Hetflejs, Tetrahedron Lett. 4787 (1971).Google Scholar
  130. 130.
    R. D. Sanner, R. G. Austin, M. S. Wrighton, W. D. Honnick, and C. U. Pittman, Jr., Inorg. Chem. 18, 928 (1979).CrossRefGoogle Scholar
  131. 131.
    J. C. Poulin, W. Dumont, T. P. Dang, and H. B. Kagan, Compt. Rend. Ser. C 277, 41 (1973).Google Scholar
  132. 132.
    J. F. Roth, J. H. Craddock, A. Hershman, and F. E. Paulik, Chem. Tech. 1,600 (1971); H. D. Grove, Hydrocarbon Proc., 76 (1972); F. E. Paulih, United States Patent No. 3769329 (1973).Google Scholar
  133. 133.
    I. V. Howell and R. D. Hancock, British Patent No.1 408 013.Google Scholar
  134. 134.
    H. Arai, T. Kanedo, and T. Kunugi, Chem. Lett. Japan, 265 (1975).Google Scholar
  135. 135.
    C. U. Pittman, Jr. and W. D. Honnick, J. Org. Chem. 45, 2132 (1980).Google Scholar
  136. 136.
    C. U. Pittman, Jr., A. Hirao, C. Jones, R. M. Hanes, and Q. Ng, Ann. N. Y. Acad. Sci. 295, 15 (1977).Google Scholar
  137. 137.
    C. U. Pittman, Jr. and C. C. Lin., J. Org. Chem. 43, 4928 (1978).Google Scholar
  138. 138.
    C. U. Pittman, Jr., W. D. Honnick, and J. J. Yang, J. Org. Chem. 45, 684 (1980).Google Scholar
  139. 139.
    C. U. Pittman, Jr. and Q. Y. Ng, United States Patent No. 4 258 206 (1981).Google Scholar
  140. 140.
    H. Arai, J. Catal. 51, 135 - 142 (1978).CrossRefGoogle Scholar
  141. 141.
    C. U. Pittman, Jr., A. Hirao, J. J. Yang, Q. Ng, R. Hanes, and C. C. Lin, Preprints Div. Petrol. Chem. (ACS) 22, 1196 (1977).Google Scholar
  142. 142.
    S. J. Fritschel, J. J. H. Ackerman, T. Keyser, and J. K. Stille, J. Org. Chem. 44, 3152 (1979).CrossRefGoogle Scholar
  143. 143.
    Badische Anilin und Soda-Fabrik A.G., French Patent No.2 053 300.Google Scholar
  144. 144.
    M. O. Farrell and C. H. VanDyke, J. Organometal. Chem. 172, 367 - 376 (1979).CrossRefGoogle Scholar
  145. 145.
    A. R. Sanger and L. R. Schallig, J. Mol. Catal. 3, 101 (1977-1978).Google Scholar
  146. 146.
    W. O. Haag and D. D. Whitehurst, “Catalysis,” edited by J. W. Hightower, paper 29, Vol. 1, p. 465 (1973).Google Scholar
  147. 147.
    R. D. Hancock, I. V. Howell, R. C. Pitkethly, and P. J. Robinson, Reference 20, 361 - 371.Google Scholar
  148. 148.
    J. M. Basset, R. Mutin, G. Descotes, and D. Sinou, Compt. Rend. Ser. C 280, 1181 (1975).Google Scholar
  149. 149.
    S. Warwel and P. Buschmeyer, Angew. Chem., Int. Ed. Engl. 17, 131-000 (1978).CrossRefGoogle Scholar
  150. 150.
    M. Terasawa, K. Kaneda, T. Smanaka, and S. Teranishi, J. Organometal. Chem. 162 (3), 403 (1978).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1983

Authors and Affiliations

  • Norman L. Holy
    • 1
  1. 1.Department of ChemistryWestern Kentucky UniversityBowling GreenUSA

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