1, 3-Dipolar additions to cyclopropenes and methylenecyclopropane

Journal of Organic Chemistry

Volumn 44, Issue 8, 1979, Pages 1202-1207

  Aue, Donald H ^a   Lorens, Robert B ^a   Helwig, Gregory S ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010412273     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo01322a003     Document Type: Article

References (82)

1. D. H. Aue, R. B. Lorens, and G. S. Helwig, Tetrahedron Lett. 4795 (1973);
2. D. H. Aue and G. S. Helwig, Tetrahedron Lett. 721 (1974).
3. R. Huisgen, Proc. Chem. Soc., London, 357 (1961);
4. R. Huisgen, Angew. Chem., Int. Ed. Engl., 2, 565 (1963).
5. R. Huisgen, R. Graskey, and J. Sauer in “The Chemistry of Alkenes”, S. Patai, Ed., Inter Science New York, 1964, p 806ff.
6. R. B. Woodward and R. Hoffmann, “The Conservation of Orbital Symmetry”, Academic Press, New York, 1971.
7. R. Huisgen, M. Seidel, G. Wallbillich, and H. Kmepfer, Tetrahedron 17, 3(1962).
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10. P. K. Kadaba, Synthesis 71 (1973).
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23. D. H. Aue, M. J. Meshishnek, and D. F. Shellhamer, Tetrahedron Lett. 4799 (1973)
24. D. H. Aue and G. S. Helwig, J. Chem. Soc., Chem. Commun. 925 (1974)
25. D. H. Aue, W. R. Davidson, and M. T. Bowers, J. Am. Chem. Soc., 98, 6700 (1976).
26. P. G. Gassman and W. J. Greenlee, J. Am. Chem. Soc., 95, 980 (1973).
27. K. B. Wiberg and W. J. Bartley, J. Am. Chem. Soc., 82, 6375 (1960).
28. M. I. Komendantov and R. R. Bekmukhametov, Zh. Org. Khim. 7, 427 (1971)
29. D. F. Eaton, R. G. Bergman, and G. S. Hammond, J. Am. Chem. Soc., 94, 1351 (1972).
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34. J. Org. Chem, 39, 63 (1974).
35. J. R. Salaün and J. M. Conia, Chem. Commun. 1579 (1971);
36. D. H. Aue, M. J. Meshishnek, and D. F. Shellhamer, Tetrahedron Lett. 4799 (1973).
37. W. Lwowski, “Nitrenes”, InterScience New York, 1970.
38. R. Huisgen, G. Szeimies, and L. Moebius, Chem. Ber., 100, 2494 (1967).
39. E. W. Garbisch, Jr., S. M. Schildcrout, D. B. Patterson, and C. M. Sprecher, J. Am. Chem. Soc., 87, 2932 (1965).
40. F. Arndt, “Organic Syntheses”, Collect. Vol. 2, Wiley, New York, 1943, p 165.
41. W. von E. Doering and C. H. DePuy, J. Am. Chem. Soc., 75, 5955 (1953).
42. D. H. Aue, R. B. Lorens, and G. S. Helwig, Tetrahedron Lett. 4795 (1973);
43. D. H. Aue and G. S. Helwig, Tetrahedron Lett. 721 (1974).
44. R. Huisgen, Proc. Chem. Soc., London, 357 (1961);
45. R. Huisgen, Angew. Chem., Int. Ed. Engl., 2, 565 (1963).
46. R. Huisgen, R. Graskey, and J. Sauer in “The Chemistry of Alkenes”, S. Patai, Ed., Inter Science New York, 1964, p 806ff.
47. R. B. Woodward and R. Hoffmann, “The Conservation of Orbital Symmetry”, Academic Press, New York, 1971.
48. R. Huisgen, M. Seidel, G. Wallbillich, and H. Kmepfer, Tetrahedron 17, 3(1962).
49. R. Huisgen and G. Steiner, J. Am. Chem. Soc., 95, 5054 (1973).
50. R. Huisgen, H. Stangl, H. J. Sturm, and H. Wagenhofer, Angew. Chem., 73, 170(1961).
51. P. K. Kadaba, Synthesis 71 (1973).
52. R. Huisgen, Angew. Chem., Int. Ed. Engl., 2, 633 (1963).
53. P. D. Bartlett, Pure Appl. Chem., 27, 597 (1971).
54. R. Huisgen and G. Steiner, Tetrahedron Lett. 3769 (1973).
55. B. M. Benjamin and C. J. Collins, J. Am. Chem. Soc., 95, 6145 (1973).
56. R. A. Firestone, J. Org. Chem, 33, 2285 (1968); J. Chem. Soc. A. 1570 (1970)
57. J. Org. Chem, 37, 2181 (1972).
58. R. Huisgen, J. Org. Chem, 33, 2291 (1968).
59. K. N. Houk, J. Sims, R. E. Duke, Jr., R. W. Strozier, and J. K. George, J. Am. Chem. Soc., 95, 7287 (1973);
60. K. N. Houk, J. Am. Chem. Soc., 94, 8953 (1972).
61. R. Sustmann and H. Trill, Angew. Chem., Int. Ed. Engl., 11, 838 (1972);
62. R. Sustmann, Pure Appl. Chem., 40, 569 (1973).
63. K. Bast, M. Christl, R. Huisgen, and W. Mack, Chem. Ber., 106, 3312 (1973).
64. D. H. Aue, M. J. Meshishnek, and D. F. Shellhamer, Tetrahedron Lett. 4799 (1973)
65. D. H. Aue and G. S. Helwig, J. Chem. Soc., Chem. Commun. 925 (1974)
66. D. H. Aue, W. R. Davidson, and M. T. Bowers, J. Am. Chem. Soc., 98, 6700 (1976).
67. P. G. Gassman and W. J. Greenlee, J. Am. Chem. Soc., 95, 980 (1973).
68. K. B. Wiberg and W. J. Bartley, J. Am. Chem. Soc., 82, 6375 (1960).
69. M. I. Komendantov and R. R. Bekmukhametov, Zh. Org. Khim. 7, 427 (1971)
70. D. F. Eaton, R. G. Bergman, and G. S. Hammond, J. Am. Chem. Soc., 94, 1351 (1972).
71. L. G. Zaitseva, L. A. Berkovich, and I. G. Bolesov, J. Org. Chem USSR (Engl. Transl.), 10, 1685 (1974).
72. J. P. Visser and P. Small, Tetrahedron Lett. 1139 (1973).
73. M. Franck-Neumann and C. Buchecker, Tetrahedron Lett. 2659 (1969).
74. J. K. Crandall and W. W. Conover, J. Chem. Soc., Chem. Commun. 33 (1973);
75. J. Org. Chem, 39, 63 (1974).
76. J. R. Salaün and J. M. Conia, Chem. Commun. 1579 (1971);
77. D. H. Aue, M. J. Meshishnek, and D. F. Shellhamer, Tetrahedron Lett. 4799 (1973).
78. W. Lwowski, “Nitrenes”, InterScience New York, 1970.
79. R. Huisgen, G. Szeimies, and L. Moebius, Chem. Ber., 100, 2494 (1967).
80. E. W. Garbisch, Jr., S. M. Schildcrout, D. B. Patterson, and C. M. Sprecher, J. Am. Chem. Soc., 87, 2932 (1965).
81. F. Arndt, “Organic Syntheses”, Collect. Vol. 2, Wiley, New York, 1943, p 165.
82. W. von E. Doering and C. H. DePuy, J. Am. Chem. Soc., 75, 5955 (1953).