Skip to main content

Part of the book series: Reactivity and Structure Concepts in Organic Chemistry ((REACTIVITY,volume 14))

Abstract

Electrophilic cleavage of aryl silanes result, in general, in specific substituted aromatic compounds in which the electrophile occupies the position to which the silyl group was previously bonded. Unlike normal electrophilic substitution reactions which involve loss of a proton, mixtures of isomers are not obtained.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
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. Kipping, F.S., Lloyd, L.L.: J. Chem. Soc. 449 (1901)

    Google Scholar 

  2. Eaborn, C.: Pure and Applied Chemistry, 19, 375 (1969)

    Article  Google Scholar 

  3. Eaborn, C., Bott, R.W., “Synthesis and Reaction of the Silicon Carbon Bond” in Organometallic Compounds of the Group IV Element, Vol I, (MacDiarmid, A.G., Ed.), p. 407–435, New York: Marcel Dekker, 1968

    Google Scholar 

  4. Bott, R.W., Eaborn, C., Greasley, P.M.: J. Chem. Soc. 4804 (1964)

    Google Scholar 

  5. Eaborn, C., Jackson, P.M., Taylor, R.: J. Chem. Soc. B, 613 (1966)

    Google Scholar 

  6. See Ref. 3, p. 410–411 and 414.

    Google Scholar 

  7. Benkeser, R.A., Krysiak, H.R.: J. Am. Chem. Soc. 76, 6353 (1954)

    Article  CAS  Google Scholar 

  8. Eaborn, C., Moore, R.C.: J. Chem. Soc. 3640 (1959)

    Google Scholar 

  9. Eaborn, C., Pande, K.C.: J. Chem. Soc. 1566 (1960)

    Google Scholar 

  10. Hillard, III, R.L., Vollhardt, K.P.C.: J. Am. Chem. Soc. 99, 4058 (1977)

    Article  CAS  Google Scholar 

  11. Hillard, III, R.L., Vollhardt, K.P.C.: Angew. Chem. Int. 16, 399 (1977)

    Article  Google Scholar 

  12. Anderson, D.G., Bradney, M.A.M., Webster, D.E.: J. Chem. Soc. B, 450 (1968)

    Google Scholar 

  13. Pray, B.O., Sommer, L.H., Goldberg, G.M., Kerr, G.T., DiGiorgio, P.A., Whitmore, F.C.: J. Am. Chem. Soc. 70, 433 (1948)

    Article  CAS  Google Scholar 

  14. Eaborn, C.: J. Chem. Soc. 2755 (1949)

    Google Scholar 

  15. Eaborn, C., Walton, D.R.M., Young, D.J.: J. Chem. Soc. B, 15 (1969)

    Google Scholar 

  16. Félix, G., Dunoguès, J., Calas, R.: Angew. Chem. Int. Ed. 18, 402 (1979)

    Google Scholar 

  17. Félix, G., Dunoguès, J., Pisciotti, F., Calas, R.: Angew. Chem. Int. Ed. 16, 488 (1977)

    Article  Google Scholar 

  18. Stock, L.M., Spector, A.R.: J. Org. Chem. 28, 3272 (1963)

    Article  CAS  Google Scholar 

  19. Koser, G.F., Wettach, R.H., Smith, C.S.: J. Org. Chem. 45, 1543 (1980)

    Article  CAS  Google Scholar 

  20. Beringer, F.M., Dehn, Jr., J.W., Winicov, M.: J. Am. Chem. Soc. 82, 2948 (1960)

    Article  CAS  Google Scholar 

  21. Ladenburg, A.: Chem. Ber. 40, 2274 (1907)

    Article  CAS  Google Scholar 

  22. Eaborn, G., Webster, D.E.: J. Chem. Soc. 179 (1960)

    Google Scholar 

  23. Eaborn, C., Steward, O.W.: Proc. Chem. Soc. 59 (1963)

    Google Scholar 

  24. Eaborn, C., Steward, O.W.: J. Chem. Soc. 521 (1965)

    Google Scholar 

  25. Sommer, L.H., Michael, K.W., Korte, W.D.: J. Am. Chem. Soc. 89, 868 (1967)

    Article  CAS  Google Scholar 

  26. Seyferth, D., White, D.L.: J. Am. Chem. Soc. 94, 3132 (1972)

    Article  CAS  Google Scholar 

  27. Nolan, S.M., Cohen, T.: J. Org. Chem. 46, 2473 (1981)

    Article  CAS  Google Scholar 

  28. Combes, C.: Compt. Rend. Acad. Sci. Paris, 122, 622 (1896)

    CAS  Google Scholar 

  29. Benkeser, R.A., Hoke, D.I., Hickner, R.A.: J. Am. Chem. Soc. 80, 5294 (1958)

    Article  Google Scholar 

  30. Bell, H.C., Kalman, J.R., Pinhey, J.T., Sternhall, S.: Tetrahedron Lett. 3391 (1974)

    Google Scholar 

  31. Taylor, E.C., Kienzle, F., Robey, R.L., McKillop, A., Hunt, J.D.: J. Am. Chem. Soc. 93, 4845 (1971)

    Article  CAS  Google Scholar 

  32. McKillop, A., Fowler, J.S., Zeleska, M.J., Hunt, J.D., Taylor, E.C., McGillivray, G.: Tetrahedron Lett. 2423 (1969)

    Google Scholar 

  33. Kalman, J.R., Pinhey, J.T., Sternhall, S.: Tetrahedron Lett. 5369 (1972)

    Google Scholar 

  34. Eaborn, C., Hashimoto, T.: Chem. and Ind. 1081 (1961)

    Google Scholar 

  35. Bott, R.W., Eaborn, C., Hashimoto, T.: J. Organometal. Chem. 3, 442 (1965)

    Article  CAS  Google Scholar 

  36. Calas, R., Bourgeois, P., Duff aut, N.: Compt. Rend, Acad. Sci. Paris, 263, C243 (1966)

    Google Scholar 

  37. Dey, K., Eaborn, C., Walton, D.R.M.: Organometal. Chem. Syn. 1, 151 (1970/71)

    Google Scholar 

  38. Austin, J.D., Eaborn, C., Smith, J.D.: J. Chem. Soc. 4744 (1963)

    Google Scholar 

  39. Sunthankar, S.V., Gilman, H.: J. Org. Chem. 15, 1200 (1950)

    Article  CAS  Google Scholar 

  40. Sakata, Y., Hashimoto, T.: Yakugaku Zasshi, 80, 728 (1960), CA 54, 24480 (1960)

    Google Scholar 

  41. Sakata, Y., Hashimoto, T.: Yakugaku Zasshi, 79, 878 (1959), CA 54, 358a (1960)

    Google Scholar 

  42. Hashimoto, T., Seki, M.: Yakugaku Zasshi, 81, 204 (1961), CA 55, 14340 (1961)

    CAS  Google Scholar 

  43. Speier, J.L.: J. Am. Chem. Soc. 75, 2930 (1953)

    Article  CAS  Google Scholar 

  44. Benkeser, R.A., Brumfield, P.E.: J. Am. Chem. Soc. 73, 4770 (1951)

    Article  CAS  Google Scholar 

  45. Benkeser, R.A., Landesman, H.: J. Am. Chem. Soc. 76, 904 (1954)

    Article  CAS  Google Scholar 

  46. Chvalovsky, V., Bazant, V.: Collect. Czech. Chem. Commun. 16, 580 (1951)

    Google Scholar 

  47. Deans, F.B., Eaborn, C.: J. Chem. Soc. 498 (1957)

    Google Scholar 

  48. Eaborn, C., Salih, Z.S., Walton, D.R.M.: J. Chem. Soc. Perkin II, 172 (1972)

    Google Scholar 

  49. Birkofer, L., Franz, M.: Chem. Ber. 104, 3062 (1971)

    Article  CAS  Google Scholar 

  50. Webb, A.F., Sethi, D.S., Gilman, H.: J. Organometal. Chem. 21, P61 (1970)

    Article  CAS  Google Scholar 

  51. Pinkerton, F.H., Thames, S.F.: J. Heterocyclic Chem. 6, 433 (1969)

    Article  CAS  Google Scholar 

  52. Pinkerton, F.H., Thames, S.F.: J. Organometal. Chem. 24, 623 (1970)

    Article  CAS  Google Scholar 

  53. Pratt, J.R., Pinkerton, F.H., Thames, S.F.: J. Organometal. Chem. 38, 29 (1972)

    Article  CAS  Google Scholar 

  54. Pinkerton, F.H., Thames, S.F.: J. Heterocyclic Chem. 8, 257 (1971)

    Article  Google Scholar 

  55. Effenberger, F., Spiegler, W.: Angew. Chem. Int. Ed. 20, 265 (1981)

    Article  Google Scholar 

  56. Pinkerton, R.H., Thames, S.F.: J. Heterocyclic Chem. 9, 67 (1972)

    Article  CAS  Google Scholar 

  57. Häbich, D., Effenberger, F.: Synthesis, 84 (1979)

    Google Scholar 

  58. Barry, A.J., Gilkey, J.W., Hook, D.E.: Ind. Eng. Chem. 51, 131 (1959)

    Article  CAS  Google Scholar 

  59. Chernyshev, E.A., Li, G.L., Petrov, A.D.: Dokl. Akad. Nauk. SSSR, 127, 808 (1959)

    CAS  Google Scholar 

  60. Petrov, A.D., Mironov, V.F., Ponomarenko, V.A., Chernyshev, E.A., Synthesis of Organosilicon Monomers, p. 288, New York: Consultants Bureau, 1964

    Google Scholar 

  61. Anderson, D.G., Bradney, M.A.M., Webster, D.E.: J. Chem. Soc. B, 450 (1968)

    Google Scholar 

  62. Félix, G., Dunoguès, J., Pisciotti, F., Calas, R.: Angew. Chem. Int. Ed. 16, 488 (1977)

    Article  Google Scholar 

  63. Chaffee, R.G., Beck, H.N.: J. Chem. and Eng. Data, 8, 453 (1963)

    Article  CAS  Google Scholar 

  64. Beck, H.N., Chaffee, R.G.: J. Chem. and Eng. Data, 8, 602 (1963)

    Article  CAS  Google Scholar 

  65. Eaborn, C., Walton, D.R.M., Young, D.J.: J. Chem. Soc. B, 15 (1969)

    Google Scholar 

  66. Matsumoto, H., Shono, K., Nagai, Y.: J. Organometal. Chem. 208, 145 (1981)

    Article  CAS  Google Scholar 

  67. Matsumoto, H., Nagashima, S., Yoshihiro, K., Nagai, Y.: J. Organometal. Chem. 85, Cl (1975)

    Article  Google Scholar 

  68. Azarian, A., Dua, S.S., Eaborn, C., Walton, D.R.M.: J. Organometal. Chem. 117, C55 (1976)

    Article  CAS  Google Scholar 

  69. Matsumoto, H., Yoshihiro, K., Nagashima, S., Watanabe, H., Nagai, Y.: J. Organometal. Chem. 128, 409 (1977)

    Article  CAS  Google Scholar 

  70. Shippey, M.A., Dervan, P.B.: J. Org. Chem. 42, 2654 (1977)

    Article  CAS  Google Scholar 

  71. Laguerre, M., Dunoguès, J., Calas, R., Duffaut, N.: J. Organometal. Chem. 112, 49 (1976)

    Article  CAS  Google Scholar 

  72. Dunoguès, J., Calas, R., Ardoin, N.: J. Organometal. Chem. 43, 127 (1972)

    Article  Google Scholar 

  73. Laguerre, M., Dunoguès, J., Calas, R.: J. Chem. Res. 8, 295 (1978)

    Google Scholar 

  74. Sakata, Y., Hashimoto, T.: Yakugaku Zasshi, 80, 728 (1960), CA 54, 24480 (1960)

    CAS  Google Scholar 

  75. Effenberger, F., Schöllkopf, K.: Angew. Chem. Int. Ed. 20, 266 (1981)

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1983 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Weber, W.P. (1983). Aryl Silanes. In: Silicon Reagents for Organic Synthesis. Reactivity and Structure Concepts in Organic Chemistry, vol 14. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-68661-0_8

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-68661-0_8

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-68663-4

  • Online ISBN: 978-3-642-68661-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics