Skip to main content

Part of the book series: Reactivity and Structure: Concepts in Organic Chemistry ((REACTIVITY,volume 7))

  • 256 Accesses

Abstract

Free radical addition and substitution reactions which have proved so useful in organic synthesis have received less attention in the synthesis of organometallic compounds. The majority of these studies have involved the main group elements and have concentrated on addition reactions. Initially particular reference was made to the addition of silanes, germanes, and various phosphorus compounds to carbon-carbon double and triple bonds [1]. More recently, reactions with more varied substrates have been studied. These include the addition of silanes to halogenated alkenes and alkynes [2, 3], e.g.

the substitution of unsaturater amines by susequent addition, elimination, e.g. [4]

addition to diphyenyldiazomethane [5] with loss of nitrogen,

and the reaction of silanes with nitroarenes to afford nitroxides, e.g. [6],

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Sosnovsky, G.: Free Radical Reactions in Preparative Organic Chemistry. New York: Macmillan 1964.

    Google Scholar 

  2. Haszeldine, R. N., Pool, C. R., Tipping, A. E.: J. C. S. Perkin I 1974, 2293.

    Google Scholar 

  3. Bevan, W. I., Haszeldine, R. N., Middleton, J., Tipping, A. E.: J. C. S. Dalton 1974, 2305.

    Google Scholar 

  4. Coy, D. H., Fitton, F., Haszeldine, R. N., Newlands, M. J., Tipping, A. E.: J. C. S. Dalton 1974, 1852.

    Google Scholar 

  5. Gaspar, P. P., Ho, C.-T., Choo, K. Y.: J. Am. Chem. Soc. 96, 7818 (1974).

    Article  CAS  Google Scholar 

  6. Cammagi, C. M., Lunazzi, L., Pedulli, G. F., Placucci, G., Tiecco, M.: J. C. S. Perkin II 1974, 1226.

    Google Scholar 

  7. McBee, E. T., Roberts, C. W., Puerckhauer, G. W. R.: J. Am. Chem. Soc. 79, 2329 (1957).

    Article  CAS  Google Scholar 

  8. Dohmaru, T., Nagata, Y., Tsurugi, J.: Bull. Chem. Soc. Japan 45, 2660 (1972).

    Article  CAS  Google Scholar 

  9. Nakao, R., Fukumoto, T., Tsurugi, J.: Bull. Chem. Soc. Japan 47, 932 (1974).

    Article  CAS  Google Scholar 

  10. Linke, K.-H., Göshausen, H. J.: Chem. Ber. 106, 3438 (1973).

    Article  CAS  Google Scholar 

  11. Brook, A. G., Duff, J. M.: Can. J. Chem. 51, 352 (1972).

    Article  Google Scholar 

  12. Komarov, N. V., Yarosh, O. G.: Bull. Acad. Sci. USSR. 1971, 1476.

    Google Scholar 

  13. Koenig, K. E., Felix, R. A., Weber, W. P.: J. Org. Chem. 39, 1539 (1974).

    Article  CAS  Google Scholar 

  14. Brook, A. G., Duff, J. M., Legrow, G. E.: J. Organometal. Chem. 122, 31 (1976).

    Article  CAS  Google Scholar 

  15. Ishikawa, M., Nakamura, A., Kumada, M.: J. Organometal. Chem. 59, C11 (1973).

    Article  CAS  Google Scholar 

  16. Rivière, P., Satgé, J.: J. Organometal. Chem. 49, 173 (1973).

    Article  Google Scholar 

  17. Voronkov, M. G., Rakhlin, V. I., Mirskov, R. G.: Proc. Acad. Sci. USSR., Chem. Div. 209, 261 (1973).

    Google Scholar 

  18. Kuivila, H. G., Sommer, R.: J. Am. Chem. Soc. 89, 5616 (1967).

    Article  CAS  Google Scholar 

  19. Jackson, R. A.: Free Radicals of Elements other than C., N, O or S. In: Free Radical Reactions. Chap. 7. Waters, W. A. (ed.). International Review of Science, Org. Chem. Ser. I, Vol. 10. London: Butterworths 1973, p. 205.

    Google Scholar 

  20. Jackson, R. A.: Free Radicals of Elements of Groups III-V. In: Free Radical Reactions. Chap. 6. Waters, W. A. (ed.). International Review of Science, Org. Chem. Ser. II, Vol. 10. London: Butterworths 1975, p. 133.

    Google Scholar 

  21. Sakurai, H.: Group IVB Radicals. In: Free Radicals. Vol. 2 Chap. 25. Kochi, J. K. (ed.). New York: Wiley-Interscience 1973, p. 741.

    Google Scholar 

  22. Maire, J.-C., van Rietschoten, J.: Helv. Chim. Acta 54, 749 (1971).

    Article  CAS  Google Scholar 

  23. Maire, J.-C., van Rietschoten, J.: Helv. Chim. Acta 54, 1054 (1971).

    Article  CAS  Google Scholar 

  24. Fish, R. H.: J. Organometal. Chem. 42, 345 (1972).

    Article  CAS  Google Scholar 

  25. Gielen, M., Nasielski, J.: Organotin Compounds. Vol. 3 Chap. 9. Sawyer, A. K. (ed). New York: Dekker 1972.

    Google Scholar 

  26. Taylor, R. D., Wardell, J. L.: J. Organometal. Chem. 77, 311 (1974).

    Article  CAS  Google Scholar 

  27. Stamm, W.: J. Org. Chem. 28, 3264 (1963).

    Article  CAS  Google Scholar 

  28. Bulten, E. J., Budding, H. A.: J. Organometal. Chem. 111, C33 (1976).

    Article  CAS  Google Scholar 

  29. Kosugi, M., Kurino, K., Takayama, K., Migita, T.: J. Organometal. Chem. 56, C11 (1973).

    Article  CAS  Google Scholar 

  30. Grignon, J., Pereyre, M.: J. Organometal. Chem. 61, C33 (1973).

    Article  CAS  Google Scholar 

  31. Rauhut, M. M., Currier, H. A., Semsel, A. M., Wystrach, V. P.: J. Org. Chem. 26, 5138 (1961).

    Article  CAS  Google Scholar 

  32. Griffin, C. E., Wells, H. J.: J. Org. Chem. 24, 2049 (1959).

    Article  CAS  Google Scholar 

  33. Griffin, C. E.: J. Org. Chem. 25, 665 (1960).

    Article  CAS  Google Scholar 

  34. Sasin, R., Olszewski, W. F., Russell, J. R., Swern, D.: J. Am. Chem. Soc. 81, 6275 (1959).

    Article  CAS  Google Scholar 

  35. Stiles, A. R., Vaughan, W. E., Rust, F. F.: J. Am. Chem. Soc. 80, 714 (1958).

    Article  CAS  Google Scholar 

  36. Preis, S., Myers, T. C., Jensen, E. V.: J. Am. Chem. Soc. 77, 6225 (1955).

    Article  CAS  Google Scholar 

  37. Laskorin, B. N., Yakshin, V. V., Bulgakova, V. B.: Zh. Obsh. Khim. 46, 2477 (1976).

    CAS  Google Scholar 

  38. Williams, R. H., Hamilton, L. A.: J. Am. Chem. Soc. 77, 3411 (1955).

    Article  CAS  Google Scholar 

  39. Topchiev, A. V., Nametkin, N. S., Solovova, O. P.: Dokl. Akad. Nauk. 86, 965 (1952).

    CAS  Google Scholar 

  40. Kosolopoff, G. M.: Organophosphorus Compounds. New York: Wiley 1950.

    Google Scholar 

  41. Kosolopoff, G. M., Maier, L.: Organic Phosphorus Compounds. Vols. 1–7. New York: Wiley 1972–1976.

    Google Scholar 

  42. Morse, J. G., Morse, K. W.: Inorg. Chem. 14, 565 (1975).

    Article  CAS  Google Scholar 

  43. Cooper, P., Fields, R., Haszeldine, R. N.: J. Chem. Soc. (C) 1971, 3031.

    Google Scholar 

  44. Brandon, R., Haszeldine, R. N., Robinson, P. J.: J. C. S. Perkin II 1973, 1301.

    Google Scholar 

  45. Laurenco, C., Burgada, R.: Tetrahedron 32, 2253 (1976).

    Article  CAS  Google Scholar 

  46. Burton, Th., Bruylants, A.: Bull. Soc. Chim. Belg. 82,131 (1973).

    Google Scholar 

  47. Burton, Th., Bruylants, A.: J. Organometal. Chem. 69, 397 (1974).

    Article  CAS  Google Scholar 

  48. Malisch, W., Kuhn, M.: Chem. Ber. 107, 2835 (1974).

    Article  CAS  Google Scholar 

  49. Motsarev, G. V., Zetkin, V. I., Inshakova, V. T., Rozenberg, V. R., Kolbasov, V. I.: Zh. Obsh. Khim. 47, 379 (1977).

    CAS  Google Scholar 

  50. Ingold, K. U., Roberts, B. P.: Free-Radical Substitution Reactions. New York: Wiley-Interscience 1971.

    Google Scholar 

  51. Davies, A. G.: Formation of Organometallic Peroxides by Autoxidation. In: Organic Peroxides. Vol. 2 Chap. 4. Swern, D. (ed.). New York: Wiley 1971, p. 337.

    Google Scholar 

  52. Sosnovsky, G., Brown, J. H.: Chem. Rev. 66, 529 (1966).

    Article  CAS  Google Scholar 

  53. Aleksandrov, Yu. A.: J. Organometal. Chem. 55, 1 (1973).

    Article  CAS  Google Scholar 

  54. Davies, A. G., Roberts, B. P.: Bimolecular Homolytic Substitution at Metal Centers. In: Free Radicals. Vol. 1 Chap. 10. Kochi, J. K. (ed.). New York: Wiley-Interscience 1973, p. 547.

    Google Scholar 

  55. Davies, A. G., Roberts, B. P., Smith, J. M.: Chem. Comm. 1970, 557.

    Google Scholar 

  56. DiGiacomo, P. M., Kuivila, H. G.: J. Organometal. Chem. 63, 251 (1973).

    Article  CAS  Google Scholar 

  57. Davies, A. G., Muggleton, B., Roberts, B. P., Tse, M.-W., Winter, J. N.: J. Organometal. Chem. 775,289(1976).

    Google Scholar 

  58. Mukaiyama, T., Takei, H.: Top. Phosphorus Chem. 1976, 587.

    Google Scholar 

  59. Dobbie, R. C.: J. Chem. Soc. (A) 1971, 2894.

    Google Scholar 

  60. Kuhn, L. P., Doali, J. O., Wellman, C.: J. Am. Chem. Soc. 82, 4792 (1960).

    Article  CAS  Google Scholar 

  61. Burg, A. B,: Acc. Chem. Res. 2, 353 (1969).

    Article  CAS  Google Scholar 

  62. Bentrude, W. G.: Phosphorus Radicals. In: Free Radicals. Vol. 2 Chap. 22. Kochi, J. K. (ed.). New York: Wiley-Interscience 1973, p. 595.

    Google Scholar 

  63. Cadogan, J. I. G.: Adv. Free Radical Chem. 2, 203 (1967).

    CAS  Google Scholar 

  64. Ang, H. G., Lien, W. S.: J. Fluorine Chem. 9, 73 (1977).

    Article  CAS  Google Scholar 

  65. Ang, H. G., Syn, Y. C.: J. Fluorine Chem. 8, 481 (1976).

    Article  CAS  Google Scholar 

  66. Ang, H. G., Ho, K. F.: J. Fluorine Chem. 8, 497 (1976).

    Article  CAS  Google Scholar 

  67. Singh, A., Gupta, V. D., Srivastava, G., Mehrotra, R. C.: J. Organometal. Chem. 64, 145 (1974).

    Article  CAS  Google Scholar 

  68. Kozhushno, B. N., Paliichuk, Yu. A., Shokol, V. A.: Zh. Obsh. Khim. 46, 2387 (1976).

    Google Scholar 

  69. Kukhar’, V. P., Sagina, E. I.: Zh. Obsh. Khim. 46, 2686 (1976).

    Google Scholar 

  70. Kharasch, M. S., Reinmuth, O.: Grignard Reactions of Non-metallic Substances. New York: Prentice-Hall 1954.

    Google Scholar 

  71. Blomberg, C.: J. Organometal. Chem. 45, 1 (1972).

    Article  CAS  Google Scholar 

  72. Brown, H. C.: Organic Synthesis via Boranes. New York: Wiley-Interscience 1975.

    Google Scholar 

  73. Elsom, L. F., Hunt, J. D., McKillop, A.: Organometal. Chem. Rev. A 8,135 (1972).

    CAS  Google Scholar 

  74. Kochi, J. K.: Oxidation-Reduction Reactions of Free Radicals and Metal Complexes. In: Free Radicals. Vol. 1 Chap. 11. Kochi, J. K. (ed.). New York: Wiley-Interscience 1973, p. 591.

    Google Scholar 

  75. Littler, J. S.: Homolytic Oxidations and Reduction of Organic Compounds by Metallic Ions. In: Free Radical Reactions. Waters, W. A. (ed.). International Review of Science. Org. Chem., Ser. I, Vol. 10. Chap. 8. London: Butterworths 1973, p. 237.

    Google Scholar 

  76. Littler, J. S., Nonhebel, D. G: Free Radical Reactions Involving Metal-containing Species and Related Processes. In: Free Radical Reactions. Waters, W. A. (ed.). International Review of Science. Org. Chem., Ser. II, Vol. 10. Chap. 8. London: Butterworths 1975, p. 211.

    Google Scholar 

  77. Brown, H. G: Boranes in Organic Chemistry. Ithaca and London: Cornell University Press 1972.

    Google Scholar 

  78. Dass Gupta, B., Funabiki, T., Johnson, M. D.: J. Am. Chem. Soc. 98, 6697 (1976).

    Article  CAS  Google Scholar 

  79. Lappert, M. F., Lednor, P. W.: Chem. Comm. 1973, 948.

    Google Scholar 

  80. Gynane, M. J. S., Lappert, M. F., Miles, S. J., Bower, P. P.: Chem. Comm. 1976, 256.

    Google Scholar 

  81. Hargreaves, N. G., Johnson, A., Puddephatt, R. J., Sutcliffe, L. H.: J. Organometal. Chem. 69, C21 (1974).

    Article  CAS  Google Scholar 

  82. Hargreaves, N. G., Puddephatt, R. J., Sutcliffe, L. H., Thompson, P. J.: Chem. Comm. 1973, 861.

    Google Scholar 

  83. Stille, J. K., Lau, K. S.: J. Am. Chem. Soc. 98, 5841 (1976).

    Article  CAS  Google Scholar 

  84. Elson, I. H., Morrell, D. G., Kochi, J. K.: J. Organometal. Chem. 84, C7 (1975).

    Article  CAS  Google Scholar 

  85. Lappert, M. F., Lednor, P. W.: Adv. Organometal. Chem. 14, 345 (1976).

    Article  CAS  Google Scholar 

  86. Kochi, J. K.: Acc. Chem. Res. 7, 351 (1974).

    Article  CAS  Google Scholar 

  87. Nefedov, V. A., Tarygina, L. K.: Zh. Org. Khim. 12, 2012 (1976).

    CAS  Google Scholar 

  88. Kondo, T., Yahamoto, K., Kumada, M.: J. Organometal. Chem. 61, 355 (1973).

    Article  CAS  Google Scholar 

  89. Kondo, T., Yahamoto, K., Kumada, M.: J. Organometal. Chem. 43, 315 (1972).

    Article  CAS  Google Scholar 

  90. Kondo, T., Yahamoto, K., Kumada, M.: J. Organometal. Chem. 35, C30 (1972).

    Article  CAS  Google Scholar 

  91. Rinehart, K. L., Jr., Michejda, G J., Kittle, P. A.: J. Am. Chem. Soc. 81, 3162 (1959).

    Article  CAS  Google Scholar 

  92. Berger, A., McEwen, W. E., Kleinberg, J.: J. Am. Chem. Soc. 83, 2274 (1961).

    Article  CAS  Google Scholar 

  93. Cais, M., Modiano, A., Raveh, A.: J. Am. Chem. Soc. 87, 5607 (1965).

    Article  CAS  Google Scholar 

  94. Cais, M., Eisenstadt, A.: J. Org. Chem. 30, 1148 (1965).

    Article  CAS  Google Scholar 

  95. Cais, M., Ashkenazi, P., Dani, S., Gottlieb, J.: J. Organometal. Chem. 122, 403 (1976).

    Article  CAS  Google Scholar 

  96. Cais, M., Ashkenazi, P., Dani, S., Gottlieb, J.: J. Organometal. Chem. 124, 49 (1977).

    Article  CAS  Google Scholar 

  97. Coyle, J. D., Marr, G.: J. Organometal. Chem. 60, 153 (1973).

    Article  CAS  Google Scholar 

  98. Nugent, W. A., Kochi, J. K.: J. Organometal. Chem. 124, 327 (1977).

    Article  CAS  Google Scholar 

  99. Nugent, W. A., Kochi, J. K.: J. Organometal. Chem. 124, 349 (1977).

    Article  CAS  Google Scholar 

  100. Nugent, W. A., Kochi, J. K.: J. Organometal. Chem. 124, 371 (1977).

    Article  CAS  Google Scholar 

  101. Larock, R. G: J. Organometal. Chem. 67, 353 (1974).

    Article  CAS  Google Scholar 

  102. Razuvaev, G. A., Ol’dekop, Yu. A., Maier, N. A.: Dokl. Akad. Nauk. 98, 613 (1954).

    CAS  Google Scholar 

  103. Emeléus, H. J., Shreeve, J. M., Spaziante, P. M.: J. Chem. Soc. (A) 1969, 431.

    Article  Google Scholar 

  104. Benner, L. S., Balch, A. L.: J. Organometal. Chem. 134, 121 (1977).

    Article  CAS  Google Scholar 

  105. Nicholson, B. K., Simpson, J.: J. Organometal. Chem. 32, C29 (1971).

    Article  CAS  Google Scholar 

  106. Berry, A. D., MacDiarmid, A. G: Inorg. Nucl. Chem. Letters 5, 601 (1969).

    Article  CAS  Google Scholar 

  107. Schmulbach, G D., Hinckley, G G, Kolich, G, Ballintine, T. A., Nassiff, P. J.: Inorg. Chem. 13, 2026 (1974).

    Article  CAS  Google Scholar 

  108. Beilin, S. L, Eliseeva, N. N., Bondarenko, G. N., Karpacheva, G. P., Dolgoplosk, B. A.: Isz. Akad. Nauk. SSSR., Ser. Khim. 1976, 2561.

    Google Scholar 

  109. Van den Bergen, A. M., West, B. O.: J. Organometal. Chem. 92, 55 (1975).

    Article  Google Scholar 

  110. Marzilli, L. G., Marzilli, P. A., Halpern, J.: J. Am. Chem. Soc. 92, 5752 (1970).

    Article  CAS  Google Scholar 

  111. Marzilli, L. G., Marzilli, P. A., Halpern, J.: J. Am. Chem. Soc. 93, 1374 (1971).

    Article  Google Scholar 

  112. Reimann, R. H., Singleton, E.: J. Organometal. Chem. 57, C75 (1973).

    Article  CAS  Google Scholar 

  113. Traverso, O., Carassiti, V., Graziani, M., Belluco, U.: J. Organometal. Chem. 57, C22 (1973).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1978 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Davies, D.I., Parrott, M.J. (1978). Organometallic Compounds. In: Free Radicals in Organic Synthesis. Reactivity and Structure: Concepts in Organic Chemistry, vol 7. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-66922-4_11

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-66922-4_11

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-66924-8

  • Online ISBN: 978-3-642-66922-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics