The cycloaddition of cyclopropenes to enones

Tetrahedron Letters

Volumn 41, Issue 21, 2000, Pages 4205-4208

  Al Dulayymi, Juma'A R ^a   Baird, Mark S ^a   Hussain, Helmi H ^b   Alhourani, Baker J ^b   Alhabashna, Al Meqdad Y ^b   Coles, Simon J ^c   Hursthouse, Michael B ^c  

^a BANGOR UNIVERSITY   (United Kingdom)

^b MUTAH UNIVERSITY   (Jordan)

^c UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENVIRONMENTAL TEMPERATURE; OXIDATION; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0034729206     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00566-9     Document Type: Article

References (32)

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2. Hussain, H. H.; Alhourani, B. J.; Al Alhabashna, M. Y. Unpublished results.
3. 2=0.1253 for 3999 unique data and 251 parameters. Full details have been deposited with the Cambridge Crystallographic Data Centre (CCDC141103).
4. Padwa, A.; Austin, D. J.; Xu, S. L. Tetrahedron Lett. 1991, 32, 4103.
5. Baird, M. S.; Hussain, H. H. Tetrahedron Lett. 1986, 27, 5143.
6. Further oxidation of the mixture of 4 and 7 with MCPBA for 18 h at 20°C led to the epoxidation of the alkene bond of 4, but left 7 unchanged.
7. For a review, see: Baird, M. S. Cyclopropanes from Cyclopropenes, in Three and Four Membered Carbocyclic Compounds; de Meijere, A., Ed.; Houben Weyl E17a, 1996; p. 114.
8. See for example: Yamauchi, M.; Katayama, S.; Baba, O.; Watanabe, T. J. Chem. Soc., Perkin Trans. 1 1990, 3041; Takaki, K.; Okada, M.; Negoro, K. J. Org. Chem. 1982, 47, 1200; Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098; Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675; Conrads, M.; Mattay, J. Chem. Ber. 1991, 124, 1425; Bakker, C. G.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays Bas 1981, 100, 13; Bridges, A. J.; Fisher, J. W. J. Org. Chem. 1984, 49, 2954; Snider, B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685; Jao, E.; Slifer, P. B.; Lalancette, R.; Hall, S. S. J. Org. Chem. 1996, 61, 2865; Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377; Takaki, K.; Yamada, M.; Negoro, K. J. Org. Chem. 1982, 47, 5246; Weinstein, B.; Lin, L.-C. C.; Fowler, F. W.; J. Org. Chem. 1980, 45, 1657; Alder, K.; Ruden, E. Chem. Ber. 1941, 74, 920; Alder, K.; Offermans, H.; Ruder, E. Chem. Ber. 1941, 74, 905; Smith, G. W.; Norden, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267, 5270.
9. See for example: Yamauchi, M.; Katayama, S.; Baba, O.; Watanabe, T. J. Chem. Soc., Perkin Trans. 1 1990, 3041; Takaki, K.; Okada, M.; Negoro, K. J. Org. Chem. 1982, 47, 1200; Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098; Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675; Conrads, M.; Mattay, J. Chem. Ber. 1991, 124, 1425; Bakker, C. G.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays Bas 1981, 100, 13; Bridges, A. J.; Fisher, J. W. J. Org. Chem. 1984, 49, 2954; Snider, B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685; Jao, E.; Slifer, P. B.; Lalancette, R.; Hall, S. S. J. Org. Chem. 1996, 61, 2865; Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377; Takaki, K.; Yamada, M.; Negoro, K. J. Org. Chem. 1982, 47, 5246; Weinstein, B.; Lin, L.-C. C.; Fowler, F. W.; J. Org. Chem. 1980, 45, 1657; Alder, K.; Ruden, E. Chem. Ber. 1941, 74, 920; Alder, K.; Offermans, H.; Ruder, E. Chem. Ber. 1941, 74, 905; Smith, G. W.; Norden, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267, 5270.
10. See for example: Yamauchi, M.; Katayama, S.; Baba, O.; Watanabe, T. J. Chem. Soc., Perkin Trans. 1 1990, 3041; Takaki, K.; Okada, M.; Negoro, K. J. Org. Chem. 1982, 47, 1200; Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098; Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675; Conrads, M.; Mattay, J. Chem. Ber. 1991, 124, 1425; Bakker, C. G.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays Bas 1981, 100, 13; Bridges, A. J.; Fisher, J. W. J. Org. Chem. 1984, 49, 2954; Snider, B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685; Jao, E.; Slifer, P. B.; Lalancette, R.; Hall, S. S. J. Org. Chem. 1996, 61, 2865; Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377; Takaki, K.; Yamada, M.; Negoro, K. J. Org. Chem. 1982, 47, 5246; Weinstein, B.; Lin, L.-C. C.; Fowler, F. W.; J. Org. Chem. 1980, 45, 1657; Alder, K.; Ruden, E. Chem. Ber. 1941, 74, 920; Alder, K.; Offermans, H.; Ruder, E. Chem. Ber. 1941, 74, 905; Smith, G. W.; Norden, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267, 5270.
11. See for example: Yamauchi, M.; Katayama, S.; Baba, O.; Watanabe, T. J. Chem. Soc., Perkin Trans. 1 1990, 3041; Takaki, K.; Okada, M.; Negoro, K. J. Org. Chem. 1982, 47, 1200; Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098; Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675;Conrads, M.; Mattay, J. Chem. Ber. 1991, 124, 1425; Bakker, C. G.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays Bas 1981, 100, 13; Bridges, A. J.; Fisher, J. W. J. Org. Chem. 1984, 49, 2954; Snider, B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685; Jao, E.; Slifer, P. B.; Lalancette, R.; Hall, S. S. J. Org. Chem. 1996, 61, 2865; Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377; Takaki, K.; Yamada, M.; Negoro, K. J. Org. Chem. 1982, 47, 5246; Weinstein, B.; Lin, L.-C. C.; Fowler, F. W.; J. Org. Chem. 1980, 45, 1657; Alder, K.; Ruden, E. Chem. Ber. 1941, 74, 920; Alder, K.; Offermans, H.; Ruder, E. Chem. Ber. 1941, 74, 905; Smith, G. W.; Norden, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267, 5270.
12. See for example: Yamauchi, M.; Katayama, S.; Baba, O.; Watanabe, T. J. Chem. Soc., Perkin Trans. 1 1990, 3041; Takaki, K.; Okada, M.; Negoro, K. J. Org. Chem. 1982, 47, 1200; Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098; Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675;Conrads, M.; Mattay, J. Chem. Ber. 1991, 124, 1425; Bakker, C. G.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays Bas 1981, 100, 13; Bridges, A. J.; Fisher, J. W. J. Org. Chem. 1984, 49, 2954; Snider, B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685; Jao, E.; Slifer, P. B.; Lalancette, R.; Hall, S. S. J. Org. Chem. 1996, 61, 2865; Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377; Takaki, K.; Yamada, M.; Negoro, K. J. Org. Chem. 1982, 47, 5246; Weinstein, B.; Lin, L.-C. C.; Fowler, F. W.; J. Org. Chem. 1980, 45, 1657; Alder, K.; Ruden, E. Chem. Ber. 1941, 74, 920; Alder, K.; Offermans, H.; Ruder, E. Chem. Ber. 1941, 74, 905; Smith, G. W.; Norden, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267, 5270.
13. See for example: Yamauchi, M.; Katayama, S.; Baba, O.; Watanabe, T. J. Chem. Soc., Perkin Trans. 1 1990, 3041; Takaki, K.; Okada, M.; Negoro, K. J. Org. Chem. 1982, 47, 1200; Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098; Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675; Conrads, M.; Mattay, J. Chem. Ber. 1991, 124, 1425; Bakker, C. G.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays Bas 1981, 100, 13; Bridges, A. J.; Fisher, J. W. J. Org. Chem. 1984, 49, 2954; Snider, B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685; Jao, E.; Slifer, P. B.; Lalancette, R.; Hall, S. S. J. Org. Chem. 1996, 61, 2865; Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377; Takaki, K.; Yamada, M.; Negoro, K. J. Org. Chem. 1982, 47, 5246; Weinstein, B.; Lin, L.-C. C.; Fowler, F. W.; J. Org. Chem. 1980, 45, 1657; Alder, K.; Ruden, E. Chem. Ber. 1941, 74, 920; Alder, K.; Offermans, H.; Ruder, E. Chem. Ber. 1941, 74, 905; Smith, G. W.; Norden, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267, 5270.
14. See for example: Yamauchi, M.; Katayama, S.; Baba, O.; Watanabe, T. J. Chem. Soc., Perkin Trans. 1 1990, 3041; Takaki, K.; Okada, M.; Negoro, K. J. Org. Chem. 1982, 47, 1200; Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098; Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675; Conrads, M.; Mattay, J. Chem. Ber. 1991, 124, 1425; Bakker, C. G.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays Bas 1981, 100, 13; Bridges, A. J.; Fisher, J. W. J. Org. Chem. 1984, 49, 2954; Snider, B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685; Jao, E.; Slifer, P. B.; Lalancette, R.; Hall, S. S. J. Org. Chem. 1996, 61, 2865; Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377; Takaki, K.; Yamada, M.; Negoro, K. J. Org. Chem. 1982, 47, 5246; Weinstein, B.; Lin, L.-C. C.; Fowler, F. W.; J. Org. Chem. 1980, 45, 1657; Alder, K.; Ruden, E. Chem. Ber. 1941, 74, 920; Alder, K.; Offermans, H.; Ruder, E. Chem. Ber. 1941, 74, 905; Smith, G. W.; Norden, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267, 5270.
15. See for example: Yamauchi, M.; Katayama, S.; Baba, O.; Watanabe, T. J. Chem. Soc., Perkin Trans. 1 1990, 3041; Takaki, K.; Okada, M.; Negoro, K. J. Org. Chem. 1982, 47, 1200; Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098; Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675; Conrads, M.; Mattay, J. Chem. Ber. 1991, 124, 1425; Bakker, C. G.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays Bas 1981, 100, 13; Bridges, A. J.; Fisher, J. W. J. Org. Chem. 1984, 49, 2954; Snider, B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685; Jao, E.; Slifer, P. B.; Lalancette, R.; Hall, S. S. J. Org. Chem. 1996, 61, 2865; Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377; Takaki, K.; Yamada, M.; Negoro, K. J. Org. Chem. 1982, 47, 5246; Weinstein, B.; Lin, L.-C. C.; Fowler, F. W.; J. Org. Chem. 1980, 45, 1657; Alder, K.; Ruden, E. Chem. Ber. 1941, 74, 920; Alder, K.; Offermans, H.; Ruder, E. Chem. Ber. 1941, 74, 905; Smith, G. W.; Norden, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267, 5270.
16. See for example: Yamauchi, M.; Katayama, S.; Baba, O.; Watanabe, T. J. Chem. Soc., Perkin Trans. 1 1990, 3041; Takaki, K.; Okada, M.; Negoro, K. J. Org. Chem. 1982, 47, 1200; Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098; Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675; Conrads, M.; Mattay, J. Chem. Ber. 1991, 124, 1425; Bakker, C. G.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays Bas 1981, 100, 13; Bridges, A. J.; Fisher, J. W. J. Org. Chem. 1984, 49, 2954; Snider, B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685; Jao, E.; Slifer, P. B.; Lalancette, R.; Hall, S. S. J. Org. Chem. 1996, 61, 2865; Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377; Takaki, K.; Yamada, M.; Negoro, K. J. Org. Chem. 1982, 47, 5246; Weinstein, B.; Lin, L.-C. C.; Fowler, F. W.; J. Org. Chem. 1980, 45, 1657; Alder, K.; Ruden, E. Chem. Ber. 1941, 74, 920; Alder, K.; Offermans, H.; Ruder, E. Chem. Ber. 1941, 74, 905; Smith, G. W.; Norden, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267, 5270.
17. See for example: Yamauchi, M.; Katayama, S.; Baba, O.; Watanabe, T. J. Chem. Soc., Perkin Trans. 1 1990, 3041; Takaki, K.; Okada, M.; Negoro, K. J. Org. Chem. 1982, 47, 1200; Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098; Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675; Conrads, M.; Mattay, J. Chem. Ber. 1991, 124, 1425; Bakker, C. G.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays Bas 1981, 100, 13; Bridges, A. J.; Fisher, J. W. J. Org. Chem. 1984, 49, 2954; Snider, B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685; Jao, E.; Slifer, P. B.; Lalancette, R.; Hall, S. S. J. Org. Chem. 1996, 61, 2865; Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377; Takaki, K.; Yamada, M.; Negoro, K. J. Org. Chem. 1982, 47, 5246; Weinstein, B.; Lin, L.-C. C.; Fowler, F. W.; J. Org. Chem. 1980, 45, 1657; Alder, K.; Ruden, E. Chem. Ber. 1941, 74, 920; Alder, K.; Offermans, H.; Ruder, E. Chem. Ber. 1941, 74, 905; Smith, G. W.; Norden, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267, 5270.
18. See for example: Yamauchi, M.; Katayama, S.; Baba, O.; Watanabe, T. J. Chem. Soc., Perkin Trans. 1 1990, 3041; Takaki, K.; Okada, M.; Negoro, K. J. Org. Chem. 1982, 47, 1200; Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098; Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675; Conrads, M.; Mattay, J. Chem. Ber. 1991, 124, 1425; Bakker, C. G.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays Bas 1981, 100, 13; Bridges, A. J.; Fisher, J. W. J. Org. Chem. 1984, 49, 2954; Snider, B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685; Jao, E.; Slifer, P. B.; Lalancette, R.; Hall, S. S. J. Org. Chem. 1996, 61, 2865; Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377; Takaki, K.; Yamada, M.; Negoro, K. J. Org. Chem. 1982, 47, 5246; Weinstein, B.; Lin, L.-C. C.; Fowler, F. W.; J. Org. Chem. 1980, 45, 1657; Alder, K.; Ruden, E. Chem. Ber. 1941, 74, 920; Alder, K.; Offermans, H.; Ruder, E. Chem. Ber. 1941, 74, 905; Smith, G. W.; Norden, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267, 5270.
19. See for example: Yamauchi, M.; Katayama, S.; Baba, O.; Watanabe, T. J. Chem. Soc., Perkin Trans. 1 1990, 3041; Takaki, K.; Okada, M.; Negoro, K. J. Org. Chem. 1982, 47, 1200; Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098; Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675; Conrads, M.; Mattay, J. Chem. Ber. 1991, 124, 1425; Bakker, C. G.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays Bas 1981, 100, 13; Bridges, A. J.; Fisher, J. W. J. Org. Chem. 1984, 49, 2954; Snider, B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685; Jao, E.; Slifer, P. B.; Lalancette, R.; Hall, S. S. J. Org. Chem. 1996, 61, 2865; Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377; Takaki, K.; Yamada, M.; Negoro, K. J. Org. Chem. 1982, 47, 5246; Weinstein, B.; Lin, L.-C. C.; Fowler, F. W.; J. Org. Chem. 1980, 45, 1657; Alder, K.; Ruden, E. Chem. Ber. 1941, 74, 920; Alder, K.; Offermans, H.; Ruder, E. Chem. Ber. 1941, 74, 905; Smith, G. W.; Norden, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267, 5270.
20. See for example: Yamauchi, M.; Katayama, S.; Baba, O.; Watanabe, T. J. Chem. Soc., Perkin Trans. 1 1990, 3041; Takaki, K.; Okada, M.; Negoro, K. J. Org. Chem. 1982, 47, 1200; Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098; Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675; Conrads, M.; Mattay, J. Chem. Ber. 1991, 124, 1425; Bakker, C. G.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays Bas 1981, 100, 13; Bridges, A. J.; Fisher, J. W. J. Org. Chem. 1984, 49, 2954; Snider, B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685; Jao, E.; Slifer, P. B.; Lalancette, R.; Hall, S. S. J. Org. Chem. 1996, 61, 2865; Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377; Takaki, K.; Yamada, M.; Negoro, K. J. Org. Chem. 1982, 47, 5246; Weinstein, B.; Lin, L.-C. C.; Fowler, F. W.; J. Org. Chem. 1980, 45, 1657; Alder, K.; Ruden, E. Chem. Ber. 1941, 74, 920; Alder, K.; Offermans, H.; Ruder, E. Chem. Ber. 1941, 74, 905; Smith, G. W.; Norden, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267, 5270.
21. See for example: Yamauchi, M.; Katayama, S.; Baba, O.; Watanabe, T. J. Chem. Soc., Perkin Trans. 1 1990, 3041; Takaki, K.; Okada, M.; Negoro, K. J. Org. Chem. 1982, 47, 1200; Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098; Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675; Conrads, M.; Mattay, J. Chem. Ber. 1991, 124, 1425; Bakker, C. G.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays Bas 1981, 100, 13; Bridges, A. J.; Fisher, J. W. J. Org. Chem. 1984, 49, 2954; Snider, B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685; Jao, E.; Slifer, P. B.; Lalancette, R.; Hall, S. S. J. Org. Chem. 1996, 61, 2865; Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377; Takaki, K.; Yamada, M.; Negoro, K. J. Org. Chem. 1982, 47, 5246; Weinstein, B.; Lin, L.-C. C.; Fowler, F. W.; J. Org. Chem. 1980, 45, 1657; Alder, K.; Ruden, E. Chem. Ber. 1941, 74, 920; Alder, K.; Offermans, H.; Ruder, E. Chem. Ber. 1941, 74, 905; Smith, G. W.; Norden, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267, 5270.
22. See for example: Yamauchi, M.; Katayama, S.; Baba, O.; Watanabe, T. J. Chem. Soc., Perkin Trans. 1 1990, 3041; Takaki, K.; Okada, M.; Negoro, K. J. Org. Chem. 1982, 47, 1200; Weichert, A.; Hoffmann, H. M. R. J. Org. Chem. 1991, 56, 4098; Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675; Conrads, M.; Mattay, J. Chem. Ber. 1991, 124, 1425; Bakker, C. G.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays Bas 1981, 100, 13; Bridges, A. J.; Fisher, J. W. J. Org. Chem. 1984, 49, 2954; Snider, B.; Phillips, G. B. J. Org. Chem. 1983, 48, 3685; Jao, E.; Slifer, P. B.; Lalancette, R.; Hall, S. S. J. Org. Chem. 1996, 61, 2865; Seebach, D.; Stucky, G.; Pfammatter, E. Chem. Ber. 1989, 122, 2377; Takaki, K.; Yamada, M.; Negoro, K. J. Org. Chem. 1982, 47, 5246; Weinstein, B.; Lin, L.-C. C.; Fowler, F. W.; J. Org. Chem. 1980, 45, 1657; Alder, K.; Ruden, E. Chem. Ber. 1941, 74, 920; Alder, K.; Offermans, H.; Ruder, E. Chem. Ber. 1941, 74, 905; Smith, G. W.; Norden, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267, 5270.
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29. C 147.0, 140.3, 129.8, 128.1, 92.2, 68.2, 23.2, 20.4, 15.3, 13.3, -3.0.
30. Baird, M. S.; Hussain, H. H.; Nethercott, W. J. Chem. Soc., Perkin Trans. 1 1986, 1845; Baird, M. S.; Dale, C. M.; Al Dulayymi, J. R. J. Chem. Soc., Perkin Trans. 1 1993, 1373.
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32. 1H NMR signal for one of the hydrogens on C-5 to the cyclopropane hydrogen on C-6. The regiochemistry of 10e and 10f was assigned by analogy to 8.