Skip to main content
Log in

Diene and dienyl complexes of iron: Reactivity and synthetic utility

  • Full Papers
  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

References

  1. A. J. Pearson,Acc. Chem. Res., 13, 463 (1980).

    Google Scholar 

  2. A. J. Birch and I. D. Jenkins, in H. Alper (Ed.),Transition Metal Organometallics in Organic Synthesis, Academic Press, New York, Vol. 1, Ch. 1, 1976.

    Google Scholar 

  3. H. Reihlen, A. Gruhl, G. von Hessling and O. Pfrengle,Liebigs. Ann. Chem., 482, 161 (1930).

    Google Scholar 

  4. J. E. Mahler and R. Pettit,J. Am. Chem. Soc., 85, 3955 (1963); G. F. Emerson, L. Watts and R. Pettit,ibid., 87, 131 (1965); G. F. Emerson and R. Pettit,ibid., 84, 4591 (1962); R. Pettit, J. C. Barborak and L. Watts,ibid., 88, 1328 (1966); C. P. Lillya and R. A. Sahatjian.J. Organometal Chem., 32, 371 (1971); R. E. Graf and C. P. Lillya,Chem. Comm., 271 (1973); T. H. Whitesides and R. W. Arhart,J. Am. Chem. Soc., 93, 5296 (1971); T. H. Whitesides, R. W. Arhart and R. W. Slaven,ibid., 95, 5792 (1973); T. H. Whitesides and J. P. Neilan,ibid., 95, 5811 (1973);98, 63 (1976); T. H. Whitesides and R. W. Slaven,J. Organometal Chem., 67, 99 (1974).

    Google Scholar 

  5. B. F. Hallam and P. L. Pauson,J. Chem. Soc., 642 (1958); R. Burton, L. Pratt and G. Wilkinson,ibid., 594 (1961).

  6. M. Franck-Neumann and D. Martina,Tetrahedron Lett., 1759 (1975).

  7. B. F. G. Johnson, J. Lewis, P. McArdle and G. L. P. Randall,J. Chem. Soc. Dalton Trans., 456 (1972).

  8. M. Franck-Neumann, F. Brian and D. Martina,Tetrahedron Lett., 5033 (1978).

  9. D. Lloyd,Carbocyclic Non-benzenoid Aromatic Compounds, Elsevier, 1966, pp. 135 and 144.

  10. D. H. R. Barton, A. A. L. Gunatilaka, T. Nakanishi, H. Patin, D. A. Widdowson and B. R. Worth,J. Chem. Soc. Perkin Trans. I, 821 (1976).

    Google Scholar 

  11. G. Evans, B. F. G. Johnson and J. Lewis,J. Organometal Chem., 102, 507 (1975).

    Google Scholar 

  12. D. H. R. Barton and H. Patin,J. Chem. Soc. Perkin Trans. I, 829 (1976).

    Google Scholar 

  13. D. M. P. Mingos,J. Chem. Soc. Dalton Trans., 20, 26, 31 (1977); M. Elian and R. Hoffmann,Inorg. Chem., 14, 1058 (1975); J. A. Connor, L. M. R. Derrick, I. H. Hillier, M. F. Guest, B. R. Higginson and D. R. Lloyd,Mol. Phys., 28, 1193 (1974).

  14. See,e.g., F. A. Cotton and J. M. Troup,J. Organometal. Chem., 77, 369 (1974); J. J. Guy, B. E. Reichert and G. M. Sheldrick,Acta Crystallogr., B32, 2504 (1976); B. F. G. Johnson, J. Lewis, D. G. Parker, P. R. Raithby, and G. M. Sheldrick,J. Organometal. Chem., 150, 115 (1978); D. A. Whiting,Cryst. Struct. Commun., 1, 379 (1972); O. S. Mills and G. Robinson,Proc. Chem. Soc., 421 (1960);Acta Crystallogr., 16, 758 (1963); M. R. Churchill and S. W.-Y. Chang,Inorg. Chem., 129, 105 (1977).

    Google Scholar 

  15. A. J. Pearson,Aust. J. Chem., 29, 1679 (1976);30, 407 (1977); H. L. Retcofsky, E. N. Frankel, and H. S. Gutowsky,J. Am. Chem. Soc., 88, 2710 (1966); H. C. Preston and J. C. Davies,ibid., 88, 1585 (1966).

    Google Scholar 

  16. A. J. Pearson and P. R. Raithby,J. Chem. Soc. Dalton Trans., (1981) in press.

  17. R. E. Graf and C. P. Lillya,J. Am. Chem. Soc., 94, 8282 (1972);J. Organometal. Chem. 47, 413 (1973); E. O. Greaves, G. R. Knox and P. L. Pauson,J. Chem. Soc. Chem. Commun., 1124 (1969).

    Google Scholar 

  18. E. O. Greaves, G. R. Knox, P. L. Pauson, S. Toma, G. A. Sim, and D. I. Woodhouse,J. Chem. Soc. Chem. Commun., 257 (1974).

  19. R. E. Graf and C. P. Lillya,J. Organometal. Chem. 122, 377 (1976).

    Google Scholar 

  20. I. Fleming in D. H. R. Barton and W. D. Ollis (Eds.),Comprehensive Organic Chemistry, Pergamon Press, Oxford, 1979, Vol. 3, p. 587.

    Google Scholar 

  21. K. N. Houk,J. Am. Chem. Soc., 95, 4092 (1973); K. N. Houk, J. Sims, R. E. Duke, jun., R. W. Strozier, and J. K. George,ibid., 95, 2787 (1973).

    Google Scholar 

  22. R. B. Woodword and R. Hoffmann,The Conservation of Orbital Symmetry, Verlag Chemie, Weinheim, 1970.

    Google Scholar 

  23. A. R. Pinhas and B. K. Carpenter,J. Chem. Soc. Chem. Commun., 15 (1980).

  24. N. S. Nametkin, A. I. Nekhaev, V. D. Tyurin and S. P. Gubin,Izv. Akad. Nauk Kaz. SSR, Ser. Khim, 676 (1975).

  25. B. F. G. Johnson, J. Lewis and D. G. Parker,J. Organometal. Chem., 141, 319 (1977).

    Google Scholar 

  26. A. J. Birch, A. J. Pearson and W. D. Raverty, unpublished results,Australian National University, 1976–77.

  27. O. A. Gansow, D. A. Schexnayder, and B. Y. Kimura,J. Am. Chem. Soc., 94, 3406 (1972).

    Google Scholar 

  28. T. H. Whitesides, R. W. Arhart, and R. W. Slaven, ref. 1; G. F. Emerson and R. Pettit, ref. 1; D. H. Gibson and R. L. Vonnahme,J. Am. Chem. Soc., 94, 5090 (1972).

    Google Scholar 

  29. A. J. Pearson,Aust. J. Chem., 29, 1841 (1976).

    Google Scholar 

  30. J. L. Roustan, J. Y. Mérour and F. Houlihan,Tetrahedron Lett., 3721 (1979).

  31. E. O. Fischer and R. D. Fischer,Angew. Chem., 72, 919 (1960).

    Google Scholar 

  32. J. E. Mahler and R. Pettit, ref. 1; J. E. Mahler, D. H. Gibson, and R. Pettit,J. Am. Chem. Soc., 85, 3959 (1963).

    Google Scholar 

  33. A. J. Birch, P. E. Cross, J. Lewis, D. A. White, and S. B. Wild,J. Chem. Soc. A, 332 (1968); A. J. Birch, K. B. Chamberlain, M. A. Haas, and D. J. Thompson,J. Chem. Soc. Perkin Trans. I, 1882 (1973).

    Google Scholar 

  34. A. J. Birch and D. H. Williamson,ibid..

    Google Scholar 

  35. A. J. Pearson and A. McElroy, unpublished data.

  36. G. A. Olah and Y. K. Mo,J. Org. Chem., 38, 353 (1973).

    Google Scholar 

  37. M. J. S. Dewar and R. C. Dougherty,The PMO Theory of Organic Chemistry, Plenum Press, New York, 1975, p. 1975, p. 19.

    Google Scholar 

  38. A. J. Birch and M. A. Haas,J. Chem. Soc. C, 2465 (1971).

    Google Scholar 

  39. A. J. Birch, K. B. Chamberlain, and D. J. Thompson,J. Chem. Soc. Perkin Trans. I, 1900 (1973).

    Google Scholar 

  40. B. F. G. Johnson, J. Lewis and D. G. Parker,J. Organometal. Chem., 127, C37 (1977).

    Google Scholar 

  41. A. J. Pearson,J. Chem. Soc. Chem. Commun., 488 (1980).

  42. A. J. Pearson and M. Chandler,Tetrahedron Lett., 21, 3933 (1980).

    Google Scholar 

  43. C. W. Ong and A. J. Pearson,ibid., 21, 2349 (1980).

    Google Scholar 

  44. A. J. Pearson and C. W. Ong,J. Chem. Soc. Perkin Trans. I, (1981) in press.

  45. D. W. Clack, M. Monshi and L. A. P. Kane-Maguire,J. Organometal. Chem. 107, C40 (1976).

    Google Scholar 

  46. R. Hoffmann and P. Hofman,J. Am. Chem. Soc., 98, 598 (1976).

    Google Scholar 

  47. A. J. Birch, P. W. Westerman, and A. J. Pearson,Aust. J. Chem., 29, 1671 (1976).

    Google Scholar 

  48. I. Fleming,Frontier Orbitals and Organic Chemical Reactions, Wiley, London, 1976.

    Google Scholar 

  49. Y. Shvo and E. Hazum,J. Chem. Soc. Chem. Commun., 336 (1974).

  50. P. T. Lansbury, R. W. Erwin, and D. A. Jeffrey,J. Am. Chem. Soc., 102, 1602 (1980); T. L. McDonald and S. Mahlingam,ibid., 102, 2113 (1980); D. Caine in R. L. Augustine (Ed.),Carbon-Carbon Bond Formation, Marcel-Dekker, New York, 1979, Vol. 1, p. 304.

    Google Scholar 

  51. A. Pelter, K. J. Gould, and L. A. P. Kane-Maguire,J. Chem. Soc. Chem. Commun., 1029 (1974).

  52. L. F. Kelly, A. S. Narula and A. J. Birch,Tetrahedron Lett., 21, 871, 2455 (1980).

    Google Scholar 

  53. A. J. Birch, A. S. Narula, P. Dahler, G. R. Stephenson, and L. F. Kelly,ibid., 21, 979 (1980).

    Google Scholar 

  54. A. J. Pearson,J. Chem. Soc. Chem. Commun., 339 (1977).

  55. A. J. Pearson,J. Chem. Soc. Perkin Trans. I, 2069 (1977).

    Google Scholar 

  56. A. J. Pearson,ibid., 1255 (1979).

    Google Scholar 

  57. E. W. Colvin, S. Malchenko, R. A. Raphael, and J. S. Roberts,ibid., 1989 (1973).

    Google Scholar 

  58. A. J. Pearson and P. R. Raithby,ibid., 395 (1980).

    Google Scholar 

  59. A. J. Pearson and C. W. Ong, unpublished data; Our original work in this area in this area contains an incorrect structure assignment: A. J. Pearson and C. W. Ong,Tetrahedron Lett., 21, 4641 (1980). This will be rectified in a forthcoming publication.

  60. A. J. Pearson, E. Mincione, M. Chandler and P. R. Raithby,J. Chem. Soc., Perkin Trans. I, 2774 (1980).

    Google Scholar 

  61. A. J. Pearson,Tetrahedron Lett., 21, 3929 (1980).

    Google Scholar 

  62. A. J. Pearson and G. C. Heywood,Tetrahedron Lett., 1645 (1981).

  63. See,e.g., T. Kametani, M. Tsubuki and H. Nemoto,J. Org. Chem., 45, 4391 (1980); T. Kametani, K. Suzuki, and H. Nemoto,ibid., 45, 2204 (1980);Idem., J. Chem. Soc. Perkin Trans. I, 2805 (1980).

    Google Scholar 

  64. E. J. Corey, M. A. Tius and J. Das,J. Am. Chem. Soc., 102, 1742 (1980); B. M. Trost, Y. Nishimura, K. Yamamoto, and S. S. McElvain,ibid., 101, 1328 (1979); J. E. McMurry, A. Andrus, G. M. Ksander, J. M. Musser and M. A. Johnson,ibid., 101, 1331 (1979).

    Google Scholar 

  65. T. Kametani, T. Honda, Y. Shiratoi and K. Fukumoto,Tetrahedron Lett., 21, 1665 (1980); G. Mock, A. B. Holmes and R. A. Raphael,ibid., 4539 (1977).

    Google Scholar 

  66. A. J. Birch, W. D. Raverty, and G. R. Stephenson,ibid., 21, 197 (1980).

    Google Scholar 

  67. A. J. Pearson,J. Chem. Soc. Perkin Trans. I, 495 (1978).

    Google Scholar 

  68. Review: J. A. Marshall, S. F. Brady and N. H. Andersen,Fortschr. Chem. Org. Naturstoffe, 31, 283 (1974).

    Google Scholar 

  69. See,e.g., S. Ito, K. Endo, T. Yoshida, M. Yatagi, and M. Kodama,J. Chem. Soc. Chem. Commun., 186 (1967); Y. Ohta and Y. Hirose,Tetrahedron Lett., 2483 (1968); J. J. Sims, W. Fenical, R. M. Wing, and P. Radlick,J. Am. Chem. Soc., 93, 3774 (1971);95, 972 (1973); A. G. González, J. Darias and J. D. Martin,Tetrahedron Lett., 2381 (1973).

  70. M. F. Semmelhack and A. Yamashita,J. Am. Chem. Soc., 102, 5924 (1980).

    Google Scholar 

  71. A. J. Pearson, P. Ham and D. C. Rees,Tetrahedron Lett., 21, 4637 (1980).

    Google Scholar 

  72. A. J. Pearson and M. Chandler,J. Chem. Soc. Perkin Trans. I, 2238 (1980).

    Google Scholar 

  73. A. J. Pearson,ibid., 400 (1980).

    Google Scholar 

  74. J. E. Baldwin,J. Chem. Soc. Chem. Commun., 734 (1976); J. E. Baldwin and L. I. Kruse,ibid., 233 (1977).

  75. A. J. Pearson and P. Ham, manuscript in preparation.

  76. See,e.g., R. H. F. Manske (Ed.),The Alkaloids, Academic Press, New York, 1973, Vol. 14.

    Google Scholar 

  77. B. Witkop,Experientia, 27, 1121 (1970).

    Google Scholar 

  78. E. J. Corey and R. A. Ruden,Tetrahedron Lett., 1495 (1973); E. J. Corey, Y. Ueda, and R. A. Ruden,ibid., 4347 (1975); E. J. Corey, M. Petrzilka and Y. Ueda,ibid., 4343 (1975); E. J. Corey, J. F. Arnett and G. N. Widiger,J. Am. Chem. Soc., 97, 430 (1975); E. J. Corey and R. D. Balanson,Heterocycles, 5, 445 (1976); T. Fukuyama, L. V. Dunkerton, M. Aratani, and Y. Kishi,J. Org. Chem., 40, 2011 (1975); M. Aratani, L. V. Dunkerton, T. Fukuyama, Y. Kishi, H. Kakoi, S. Sugiura and S. Inoue,ibid., 40, 2009 (1975); H. E. Schoemaker and W. N. Speckamp,Tetrahedron Lett., 1515 (1978);Tetrahedron, 36, 951 (1980); E. Gossinger, R. Imhof and H. Wehrli,Helv. Chim. Acta, 58, 96 (1975).

  79. S. M. Weinreb and M. F. Semmelhack,Acc. Chem. Res., 8, 158 (1975), and refs. therein; T. A. Bryson and C. A. Wilson,Synth. Commun., 6, 521 (1976).

    Google Scholar 

  80. G. Stork and J. E. Dolfini,J. Am. Chem. Soc., 85, 2872 (1963).

    Google Scholar 

  81. Review: G. A. Cordell in R. H. F. Manske and R. Rodrigo (Eds.),The Alkaloids, Academic Press, New York, Vol. 17, 1979, Ch 3.

    Google Scholar 

  82. A. J. Pearson and D. C. Rees,Tetrahedron Lett., 21, 3937 (1980).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pearson, A.J. Diene and dienyl complexes of iron: Reactivity and synthetic utility. Transition Met Chem 6, 67–78 (1981). https://doi.org/10.1007/BF00626109

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00626109

Keywords

Navigation