Transition-Metal-Catalyzed Acetylene Cyclizations in Organic Synthesis

Accounts of Chemical Research

Volumn 10, Issue 1, 1977, Pages 1-8

  Vollhardt, K Peter C ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001800335     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar50109a001     Document Type: Article

References (79)

1. S. W. Benson, “Thermochemical Kinetics”, Wiley, New York, N.Y., 1968
2. M. Berthelot, C. R. Hebd. Seances Acad. Sci., 62, 905 (1866)
3. J. A. Nieuwland and R. R. Vogt, “The Chemistry of Acetylene”, Reinhold, New York, N.Y., 1945
4. G. M. Badger, G. E. Lewis, and I. M. Napier, J. Chem. Soc., 2825 (1960)
5. H. G. Viehe, “Chemistry of Acetylenes”, Marcel Dekker, New York, N.Y., 1969
6. K. P. C. Vollhardt, Top. Curr. Chem., 59,276 (1975)
7. W. Reppe, O. Schlichting, K. Klager, and T. Toepel, Justus Liebigs Ann. Chem., 560, 1 (1948)
8. C. W. Bird, “Transition Metal Intermediates in Organic Synthesis”,Chapter 1, Logos Press, London, 1967
9. U. Kruerke, C. Hoogzand, and W. Hübei, Chem. Ber., 94, 2817 (1961)
10. F. L. Bowden and A. B. P. Lever, Organomet. Chem. Rev., 3, 227 (1968)
11. K. Sonogashira and N. Hagihara, Bull. Chem. Soc. Jpn., 39,1178 (1966)
12. G. Fachinetti and C. Floriani, J. Chem. Soc.,Chem. Commun., 66 (1974)
13. J. A. Labinger, J. Schwartz, and J. M. Townsend, J. Am. Chem. Soc., 96, 4009 (1974)
14. K. L. T. Wong, J. L. Thomas, and H. H. Brintziner, J. Am. Chem. Soc., 96, 3694 (1974)
15. D. W. Hart, T. F. Blackburn, and J. Schwartz, J. Am. Chem. Soc., 97, 679 (1975)
16. J. A. Labinger and J. Schwartz, J. Am. Chem. Soc., 97,1596 (1975)
17. R. J. Klingler, W. Butler, and M. D. Curtis, J. Am. Chem. Soc., 97, 3535(1975)
18. A. J. Hubert and J. Dale, J. Chem. Soc., 3160 (1965)
19. E. S. Colthup and L. S. Meriwether, J. Org. Chem., 26, 5169 (1961)
20. R. S. Macomber, J. Org. Chem., 38, 816 (1973)
21. R. B. King, I. Haiduc, and C. W. Eavenson, J. Am. Chem. Soc., 95, 2508 (1973)
22. H. B. Chin and R. Bau, J. Am. Chem. Soc., 95, 5068 (1973)
23. R. B. King and A. Efraty, J. Am. Chem. Soc., 94, 3021 (1972)
24. R. B. King and M. N. Ackermann, J. Organomet. Chem., 67, 431 (1974)
25. R. B. King, I. Haiduc, and A. Efraty, J. Organomet. Chem., 47,145 (1973)
26. E. Müller, C. Beissner, H. Jakle, E. Danger, H. Muhm, G. Odenigbo, M. Sauerbier, A. Segnitz, D. Streichfuss, and R. Thomas, Justus Liebigs Ann. Chem., 754, 64 (1971)
27. E. Müller, Synthesis, 761 (1974)
28. C. W. Bird, J. Organomet. Chem., 47, 281 (1973)
29. E. Müller, A. Scheller, W. Winter, F. Wagner, and H. Meier, Chem. Ztg., 99, 155 (1975)
30. F. Wagner and H. Meier, Tetrahedron, 30, 773 (1974)
31. J. Hambrecht, H. Straub, and E. Müller, Tetrahedron Lett., 1789 (1976)
32. A. J. Hubert and M. Hubert, Tetrahedron Lett., 5779 (1966)
33. A. J. Hubert, J. Chem. Soc. C. 6, 11, 13, 1984 (1967)
34. R. D. Stephens, J. Org. Chem., 38, 2260 (1973)
35. R. L. Hillard III and K. P. C. Vollhardt, Angew. Chem., 87, 744 (1975)
36. R. L. Hillard III and K. P. C. Vollhardt, Angew. Chem., Int. Ed. Engl., 14, 712 (1975)
37. R. L. Hillard III and K. P. C. Vollhardt, J. Am. Chem. Soc., submitted for publication
38. J. Bernard, R. Paul, M. Boiron, C. Jacquillat, and R. Maral, Ed., “Rubidomycin”, Springer-Verlag, New York, N.Y., 1969
39. A. S. Kende, Y. Tsay, and J. E. Mills, J. Am. Chem. Soc., 98, 1967 (1976)
40. M. P. Cava and M. J. Mitchell, “Cyclobutadiene and Related Compounds”, Academic Press, New York, N.Y., 1967
41. W. Oppolzer, J. Am. Chem. Soc., 93, 3833 (1971)
42. W. Oppolzer and K. Keller, J. Am. Chem. Soc., 93, 3836 (1971)
43. W. Oppolzer, Angew. Chem., Int. Ed. Engl., 11, 1031 (1972)
44. R. Hug, H.-J. Hansen, and H. Schmid, Helo. Chim. Acta, 55,10 (1972)
45. P. G. Sammes, Tetrahedron, 32, 405 (1976)
46. W. Oppolzer, Tetrahedron Lett., 1001 (1974)
47. T. Kametani and K. Fukumoto, Heterocycles, 3, 29 (1975)
48. T. Kametani, Y. Kato, T. Honda, and K. Fukumoto, Heterocycles, 4, 241 (1976)
49. T. Kametani, H. Nemoto, H. Ishikawa, K. Shiroyama, and K. Fukumoto, J. Am. Chem. Soc., 98, 3378 (1976)
50. I. L. Klundt, Chem. Rev., 70, 471 (1970)
51. K. P. C. Vollhardt and R. G. Bergman, J. Am. Chem. Soc., 96, 4996 (1974)
52. W. G. L. Aalbersberg, A. J. Barkovich, R. L. Funk, R. L. Hillard III, and K. P. C. Vollhardt, J. Am. Chem. Soc., 97, 5600 (1975)
53. J. P. Coliman, J. W. Kang, W. F. Little, and M. F. Sullivan, Inorg. Chem., 7, 1298 (1968)
54. J. P. Coliman, Acc. Chem. Res., 1, 136 (1968)
55. P. M. Maitlis, Pure Appl. Chem., 30, 427 (1972)
56. P. M. Maitlis, Pure Appl. Chem., 33, 489 (1973)
57. P. M. Maitlis, Acc. Chem. Res., 9, 93 (1976)
58. H. Yamazaki and N. Hagihara, J. Organomet. Chem., 21,431 (1970)
59. S. A. Gardner, P. S. Andrews, and M. D. Rausch, Inorg. Chem., 12, 2396 (1973)
60. L. S. Meriwether, M. F. Leto, E. C. Colthup, and G. W. Kennerly, J. Org. Chem., 27, 3930 (1962)
61. K. P. C. Vollhardt, J. E. Bercaw, and R. G. Bergman, J. Am. Chem. Soc., 96, 4998 (1974)
62. K. P. C. Vollhardt, J. E. Bercaw, and R. G. Bergman, J. Organometal. Chem., 97, 283 (1975)
63. C. Eaborn, J. Organometal. Chem., 100, 43 (1975)
64. D. Seyferth and D. L. White,J. Am. Chem. Soc., 94, 3132 (1972)
65. R. L. Funk and K. P. C. Vollhardt, J. Chem. Soc., Chem. Commun., 833 (1976)
66. T. Kametani, M. Kajiwara, T. Takahashi, and K. Fukumoto, Tetrahedron, 31, 949 (1975)
67. R. L. Funk and K. P. C. Vollhardt, J. Am. Chem. Soc., 98, 6755 (1976)
68. H. Christol, A. Gaven, Y. Pietrasanta, and J. L. Vernet, Bull. Soc. Chim. Fr., 4510 (1971)
69. Y. Wakatsuki and H. Yamazaki, Synthesis, 26 (1976)
70. H. Bonnemann and R. Brinkman, Synthesis, 600 (1975)
71. J. C. Godfrey in E. Klingsberg, Ed., “Pyridine and Its Derivatives”, Part III, Interscience, New York, N.Y., 1962, p 347
72. M. O. Riley and J. D. Park, Tetrahedron Lett., 2871 (1971)
73. R. P. Thummel, J. Chem. Soc., Chem. Commun., 899 (1974)
74. E. Cuthbertson and D. D. MacNicol, Tetrahedron Lett., 1893 (1975)
75. A. J. Barkovich and K. P. C. Vollhardt, J. Am. Chem. Soc., 98,2667 (1976)
76. R. L. Hillard III and K. P. C. Vollhardt, J. Am. Chem. Soc., 98,3579 (1976)
77. R. L. Funk and K. P. C. Vollhardt, Angew. Chem., Int. Ed. Engl., 15, 53 (1976)
78. C. J. Saward and K. P. C. Vollhardt, Tetrahedron Lett., 4539 (1975)
79. D. Davalian and P. J. Garratt, J. Am. Chem. Soc., 97, 6883 (1975)