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Electrophilic Additions to Carbon-Carbon Multiple Bonds

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Advanced Organic Chemistry

Part of the book series: Advanced Organic Chemistry ((AOCB))

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General References

Addition of Hydrogen Halide, Halogens, and Related Electrophiles

  • P. B. De la Mare and R. Bolton, Electrophilic Addition to Unsaturated Systems, Elsevier, Amsterdam, 1982.

    Google Scholar 

  • R. C. Fahey, Top Stereochem. 2:237 (1968).

    Google Scholar 

Solvomercuration

Addition of Sulfur and Selenium Reagents

  • D. J. Clive, Tetrahedron 34:1049 (1978).

    Article  CAS  Google Scholar 

  • D. Liotta, ed., Organoselenium Chemistry, John Wiley & Sons, New York, 1987.

    Google Scholar 

  • S. Patai and Z. Rappoport, ed., The Chemistry of Organic Selenium and Tellurium Compounds, Johnn Wiley & Sons, New York, 1986.

    Google Scholar 

  • C. Paulmier, Selenium Reagents and Intermediates in Organic Synthesis, Pergamon, Oxford, 1986.

    Google Scholar 

Additions to Acetylenes and Allenes

  • T. F. Rutledge, Acetylenes and Allenes, Reinhold, New York, 1969.

    Google Scholar 

  • G. H. Schmid, in The Chemistry of the Carbon-Carbon Triple Bond, S. Patai, ed., John Wiley & Sons, New York, 1978, Chapter 8.

    Google Scholar 

  • L. Brandsma, Preparative Acetylenic Chemistry, 2nd ed. Elsevier, Amsterdam, 1988.

    Google Scholar 

Organoboranes as Synthetic Intermediates

  • H. C. Brown, Organic Synthese via Boranes, John Wiley & Sons, New York, 1975.

    Google Scholar 

  • G. Cragg, Organoboranes in Organic Synthesis, Marcel Dekker, New York, 1973.

    Google Scholar 

  • A. Pelter, K. Smith, and H. C. Brown, Borane Reagents, Academic Press, New York, 1988.

    Google Scholar 

Problems

  1. N. Kharasch and C. M. Buess, J. Am. Chem. Soc. 71:2724 (1949).

    Article  CAS  Google Scholar 

  2. I. Heilbron, E. R. H. Jones, M. Julia, and B. C. L. Weedon, J. Chem. Soc. 1949:1823.

    Google Scholar 

  3. A. J. Sisti, J. Org. Chem. 33:3953 (1968).

    CAS  Google Scholar 

  4. H. C. Brown and G. Zweifel, J. Am. Chem. Soc. 83:1241 (1961).

    CAS  Google Scholar 

  5. F. W. Fowler, A. Hassner, and L. A. Levy, J. Am. Chem. Soc. 89:2077 (1967).

    Article  CAS  Google Scholar 

  6. A. Hassner and F. W. Fowler, J. Org. Chem. 33:2686 (1968).

    Article  CAS  Google Scholar 

  7. A. Padwa, T. Blacklock, and A. Tremper, Org. Synth. 57:83 (1977).

    CAS  Google Scholar 

  8. I. Ryu, S. Murai, I. Niwa, and N. Sonoda, Synthesis 1977:874.

    Google Scholar 

  9. R. A. Amos and J. A. Katzenellenbogen, J. Org. Chem. 43:560 (1978).

    CAS  Google Scholar 

  10. H. C. Brown and G. J. Lynch, J. Org. Chem. 46:531 (1981).

    CAS  Google Scholar 

  11. R. C. Cambie, R. C. Hayward, P. S. Rutledge, T. Smith-Palmer, B. E. Swedlund, and P. D. Woodgate, J. Chem. Soc, Perkin Trans. 1 1979:180.

    Google Scholar 

  12. l. A. B. Holmes, K. Russell, E. S. Stern, M. E. Stubbs, and N. K. Welland, Tetrahedron Lett. 25:4183 (1984).

    Google Scholar 

  13. N. S. Zefirov, T. N. Velikokhat’ko, and N. K. Sadovaya, Zh. Org. Khim. (Engl. trans.) 19:1407 (1983).

    Google Scholar 

  14. F. B. Gonzalez and P. A. Bartlett, Org. Synth. 64:175 (1985).

    Google Scholar 

  15. D. J. Pasto and J. A. Gontarz, J. Am. Chem. Soc. 91:2147 (1969).

    Google Scholar 

  16. D. J. Pasto and C. C. Cumbo, J. Am. Chem. Soc. 86:4343 (1964).

    Google Scholar 

  17. D. J. Pasto and J. A. Gontarz, J. Am. Chem. Soc. 93:6902 (1971).

    CAS  Google Scholar 

  18. R. Gleiter and G. Müller, J. Org. Chem. 53:3912 (1988).

    CAS  Google Scholar 

  19. G. Stork and R. Borch, J. Am. Chem. Soc. 86:935 (1964).

    CAS  Google Scholar 

  20. T. Hori and K. B. Sharpless, J. Org. Chem. 43:1689 (1978).

    CAS  Google Scholar 

  21. E. Kloster-Jensen, E. Kovats, A. Eschenmoser, and E. Heilbronner, Helv. Chim. Acta 39:1051 (1956).

    CAS  Google Scholar 

  22. P. N. Rao, J. Org. Chem. 36:2426 (1971).

    Article  CAS  Google Scholar 

  23. R. A. Moss and E. Y. Chen, J. Org.Chem. 46:1466 (1981).

    CAS  Google Scholar 

  24. J. M. Jerkunica and T. G. Traylor, Org. Synth. 53:94 (1973).

    CAS  Google Scholar 

  25. G. Zweifel and C. C. Whitney, J. Am. Chem. Soc. 89:2753 (1967).

    CAS  Google Scholar 

  26. R. E. Ireland and P. Bey, Org. Synth. 53:63 (1973).

    CAS  Google Scholar 

  27. W. I. Fanta and W. F. Erman, J. Org. Chem. 33:1656 (1968).

    Article  CAS  Google Scholar 

  28. W. E. Billups, J. H. Cross, and C. V Smith, J. Am. Chem. Soc. 95:3438 (1973).

    CAS  Google Scholar 

  29. G. W. Kabalka and E. E. Gooch III, J. Org. Chem. 45:3578 (1980).

    CAS  Google Scholar 

  30. E. J. Corey, G. Wess, Y. B. Xiang, and A. K. Singh, J. Am. Chem. Soc. 109:4717 (1987).

    CAS  Google Scholar 

  31. I. Nakatsuka, N. L. Ferreira, W. C. Eckelman, B. E. Francis, W. J. Rzeszotarski, R. E. Gibson, E. M. Jagoda, and R. C. Reba, J. Med. Chem. 27:1287 (1984).

    Article  CAS  Google Scholar 

  32. W. Oppolzer, H. Hauth, P. Pfaffli, and R. Wenger, Helv. Chim. Acta 60:1801 (1977).

    CAS  Google Scholar 

  33. G. H. Posner and P. W. Tang, J. Org. Chem. 43:4131 (1978).

    Article  CAS  Google Scholar 

  34. A. V Bayquen and R. W. Read, Tetrahedron 52:13467 (1996).

    Article  CAS  Google Scholar 

  35. T. Fukuyama and G. Liu, J. Am. Chem. Soc. 118:7426 (1996).

    Article  CAS  Google Scholar 

  36. E. J. Corey and H. Estreicher, J. Am. Chem. Soc. 100:6294 (1978).

    CAS  Google Scholar 

  37. E. J. Corey and H. Estreicher, Tetrahedron Lett. 1980:1113.

    Google Scholar 

  38. G. A. Olah and M. Nohima, Synthesis 1973:785.

    Google Scholar 

  39. D. J. Pasto and F. M. Klein, Tetrahedron Lett. 1967:963.

    Google Scholar 

  40. H. J. Reich, J. M. Renga, and I. L. Reich, J. Am. Chem. Soc. 97:5434 (1975).

    CAS  Google Scholar 

  41. H. C. Brown, G. J. Lynch, W. J. Hammar, and L. C. Liu, J. Org. Chem. 44:1910 (1979).

    CAS  Google Scholar 

  42. P. A. Bartlett and J. Myerson, J. Am. Chem. Soc. 100:3950 (1978).

    CAS  Google Scholar 

  43. R. Lavilla, O. Coll, M. Nicolas, and J. Bosch, Tetrahedron Lett. 39:5089 (1998).

    Article  CAS  Google Scholar 

  44. A. Garofalo, M. B. Hursthouse, K. M. A. Malik, H. F. Olivio, S. M. Roberts, and V Sik, J. Chem. Soc, Perkin Trans. 1 1994:1311.

    Google Scholar 

  45. H. Imagawa, T. Shigaraki, T. Suzuki, H. Takao, H. Yamada, T. Sugihara, and M. Nichizawa, Chem. Pharm. Bull. 46:1341 (1998).

    CAS  Google Scholar 

  46. A. G. Schultz and S. J. Kirmich, J. Org. Chem. 61:5626 (1996).

    CAS  Google Scholar 

  47. I. Fleming and N. J. Lawrence, J. Chem. Soc, Perkin Trans. 1 1992:3309; 1998:2679.

    Google Scholar 

  48. R. Bittman, H.-S. Byun, K. C. Reddy, P. Samadder, and G. Arthur, J. Med. Chem. 40:1391 (1997).

    Article  CAS  Google Scholar 

  49. D. A. Evans, J. E. Ellman, and R. L. Dorow, Tetrahedron Lett. 28:1123 (1987).

    CAS  Google Scholar 

  50. K. C. Nicolaou, R. L. Magolda, W. J. Sipio, W. E. Barnette, Z. Lysenko, and M. M. Joullie, J. Am. Chem. Soc. 102:3784 (1980).

    CAS  Google Scholar 

  51. K. C. Nicolaou, W. E. Barnette, and R. L. Magolda, J. Am. Chem. Soc. 103:3472 (1981).

    CAS  Google Scholar 

  52. S. Knapp, A. T. Levorse, and J. A. Potenza, J. Org. Chem. 53:4773 (1988).

    CAS  Google Scholar 

  53. T. H. Jones and M. S. Blum, Tetrahedron Lett. 22:4373 (1981).

    CAS  Google Scholar 

  54. W. T. Smith and G. L. McLeod, Org. Synth. IV:345 (1963).

    Google Scholar 

  55. K. E. Harding, T. H. Marman, and D. Nam, Tetrahedron Lett. 29:1627 (1988).

    CAS  Google Scholar 

  56. S. Terahima, M. Hayashi, and K. Koga, Tetrahedron Lett. 1980:2733.

    Google Scholar 

  57. A. Toshimitsu, K. Terao, and S. Uemura, J. Org. Chem. 51:1724 (1986).

    Article  CAS  Google Scholar 

  58. W. Oppolzer and P. Dudfield, Tetrahedron Lett. 26:5037 (1985); D. A. Evans, J. A. Ellman, and R. L. Dorow, Tetrahedron Lett. 28:1123 (1987).

    CAS  Google Scholar 

  59. T. W. Bell, J. Am. Chem. Soc. 103:1163 (1981).

    Article  CAS  Google Scholar 

  60. H. C. Brown and B. Singaran, J. Am. Chem. Soc. 106:1794 (1984).

    Google Scholar 

  61. S. Masamune, B. M. Kim, J. S. Petersen, T. Sato, S. J. Veenstra, and T. Imai, J. Am. Chem. Soc. 107:4549 (1985).

    CAS  Google Scholar 

  62. C. F. Palmer, K. D. Parry, S. M. Roberts, and V Sik, J. Chem. Soc, Perkin Trans. 1 1992:1021; C. F. Palmer and R. McCague, J. Chem. Soc, Perkin Trans. 1 1998:2977; A. Toyota, A. Nishimura, and C. Kaneko, Heterocycles 45:2105 (1997).

    Google Scholar 

  63. M. Noguchi, H. Okada, M. Watanabe, K. Okuda, and O. Nakamura, Tetrahedron 52:6581 (1996).

    CAS  Google Scholar 

  64. R. Madsen, C. Roberts, and B. Fraser-Reid, J. Org. Chem. 60:7920 (1995).

    CAS  Google Scholar 

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© 2002 Kluwer Academic Publishers

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(2002). Electrophilic Additions to Carbon-Carbon Multiple Bonds. In: Advanced Organic Chemistry. Advanced Organic Chemistry. Springer, Boston, MA. https://doi.org/10.1007/0-306-47380-1_4

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  • DOI: https://doi.org/10.1007/0-306-47380-1_4

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-0-306-46244-3

  • Online ISBN: 978-0-306-47380-7

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