Bridged and superbridged cyclopropenylidene iminium salts

Tetrahedron Letters

Volumn 40, Issue 44, 1999, Pages 7769-7772

  Schuster, Andreea ^a   Rominger, Frank ^a   Gleiter, Rolf ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Cyclophanes; Cyclopropenones; Iminium salts

Indexed keywords

AMINE; CYCLOPROPANE DERIVATIVE; FUSED ALICYCLIC AROMATIC COMPOUND; IMINE; ORGANOBORON DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; SYNTHESIS;

EID: 0033615773     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01660-3     Document Type: Article

References (26)

1. 1. Reviews: Krebs, A.; Angew. Chem. 1965, 77, 10; Yoshida, Z.; Top. Curr. Chem. 1973, 40, 47; Eicher, T.; Weber, J. L.; Top. Curr. Chem. 1975, 57, 1; Banwell, M. G.; Halton B. in The Chemistry of the Cyclopropyl Group, Part 2, Ed.: Rappoport, Z. 1987, John Wiley & Sons; Carbocyclic Three and Four-Membered Ring Compounds in Methoden der Organischen Chemie (Houben-Weyl), Ed.: de Meijere, A.: Vol. E 17d, G. Thieme, Stuttgart 1997.
2. 1. Reviews: Krebs, A.; Angew. Chem. 1965, 77, 10; Yoshida, Z.; Top. Curr. Chem. 1973, 40, 47; Eicher, T.; Weber, J. L.; Top. Curr. Chem. 1975, 57, 1; Banwell, M. G.; Halton B. in The Chemistry of the Cyclopropyl Group, Part 2, Ed.: Rappoport, Z. 1987, John Wiley & Sons; Carbocyclic Three and Four-Membered Ring Compounds in Methoden der Organischen Chemie (Houben-Weyl), Ed.: de Meijere, A.: Vol. E 17d, G. Thieme, Stuttgart 1997.
3. 1. Reviews: Krebs, A.; Angew. Chem. 1965, 77, 10; Yoshida, Z.; Top. Curr. Chem. 1973, 40, 47; Eicher, T.; Weber, J. L.; Top. Curr. Chem. 1975, 57, 1; Banwell, M. G.; Halton B. in The Chemistry of the Cyclopropyl Group, Part 2, Ed.: Rappoport, Z. 1987, John Wiley & Sons; Carbocyclic Three and Four-Membered Ring Compounds in Methoden der Organischen Chemie (Houben-Weyl), Ed.: de Meijere, A.: Vol. E 17d, G. Thieme, Stuttgart 1997.
4. 1. Reviews: Krebs, A.; Angew. Chem. 1965, 77, 10; Yoshida, Z.; Top. Curr. Chem. 1973, 40, 47; Eicher, T.; Weber, J. L.; Top. Curr. Chem. 1975, 57, 1; Banwell, M. G.; Halton B. in The Chemistry of the Cyclopropyl Group, Part 2, Ed.: Rappoport, Z. 1987, John Wiley & Sons; Carbocyclic Three and Four-Membered Ring Compounds in Methoden der Organischen Chemie (Houben-Weyl), Ed.: de Meijere, A.: Vol. E 17d, G. Thieme, Stuttgart 1997.
5. 1. Reviews: Krebs, A.; Angew. Chem. 1965, 77, 10; Yoshida, Z.; Top. Curr. Chem. 1973, 40, 47; Eicher, T.; Weber, J. L.; Top. Curr. Chem. 1975, 57, 1; Banwell, M. G.; Halton B. in The Chemistry of the Cyclopropyl Group, Part 2, Ed.: Rappoport, Z. 1987, John Wiley & Sons; Carbocyclic Three and Four-Membered Ring Compounds in Methoden der Organischen Chemie (Houben-Weyl), Ed.: de Meijere, A.: Vol. E 17d, G. Thieme, Stuttgart 1997.
6. 2. Breslow, R.; Yuan, C.; J. Am. Chem. Soc. 1958, 80, 5991; Tobey. S. W.; West, R.; J. Am. Chem. Soc. 1964, 86, 1459; Breslow, R.; Altman, L. J.; Krebs, A.; Mohacsi, E.; Murata, I.; Peterson, R. A.: Posner. J., J. Am. Chem. Soc. 1965, 87, 1326; Farnum, D. G.; Mehta, G.; Silberman, R. G., J. Am. Chem. Soc. 1967, 89, 5048; Breslow, R.; Haynie, R.; Mirra, J.; J. Am. Chem. Soc. 1959, 81, 247; Vol'pin, M. E.; Koreshkov, Yu. D.; Kursanov, D. N.; Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1959, 3, 560.
7. 2. Breslow, R.; Yuan, C.; J. Am. Chem. Soc. 1958, 80, 5991; Tobey. S. W.; West, R.; J. Am. Chem. Soc. 1964, 86, 1459; Breslow, R.; Altman, L. J.; Krebs, A.; Mohacsi, E.; Murata, I.; Peterson, R. A.: Posner. J., J. Am. Chem. Soc. 1965, 87, 1326; Farnum, D. G.; Mehta, G.; Silberman, R. G., J. Am. Chem. Soc. 1967, 89, 5048; Breslow, R.; Haynie, R.; Mirra, J.; J. Am. Chem. Soc. 1959, 81, 247; Vol'pin, M. E.; Koreshkov, Yu. D.; Kursanov, D. N.; Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1959, 3, 560.
8. 2. Breslow, R.; Yuan, C.; J. Am. Chem. Soc. 1958, 80, 5991; Tobey. S. W.; West, R.; J. Am. Chem. Soc. 1964, 86, 1459; Breslow, R.; Altman, L. J.; Krebs, A.; Mohacsi, E.; Murata, I.; Peterson, R. A.: Posner. J., J. Am. Chem. Soc. 1965, 87, 1326; Farnum, D. G.; Mehta, G.; Silberman, R. G., J. Am. Chem. Soc. 1967, 89, 5048; Breslow, R.; Haynie, R.; Mirra, J.; J. Am. Chem. Soc. 1959, 81, 247; Vol'pin, M. E.; Koreshkov, Yu. D.; Kursanov, D. N.; Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1959, 3, 560.
9. 2. Breslow, R.; Yuan, C.; J. Am. Chem. Soc. 1958, 80, 5991; Tobey. S. W.; West, R.; J. Am. Chem. Soc. 1964, 86, 1459; Breslow, R.; Altman, L. J.; Krebs, A.; Mohacsi, E.; Murata, I.; Peterson, R. A.: Posner. J., J. Am. Chem. Soc. 1965, 87, 1326; Farnum, D. G.; Mehta, G.; Silberman, R. G., J. Am. Chem. Soc. 1967, 89, 5048; Breslow, R.; Haynie, R.; Mirra, J.; J. Am. Chem. Soc. 1959, 81, 247; Vol'pin, M. E.; Koreshkov, Yu. D.; Kursanov, D. N.; Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1959, 3, 560.
10. 2. Breslow, R.; Yuan, C.; J. Am. Chem. Soc. 1958, 80, 5991; Tobey. S. W.; West, R.; J. Am. Chem. Soc. 1964, 86, 1459; Breslow, R.; Altman, L. J.; Krebs, A.; Mohacsi, E.; Murata, I.; Peterson, R. A.: Posner. J., J. Am. Chem. Soc. 1965, 87, 1326; Farnum, D. G.; Mehta, G.; Silberman, R. G., J. Am. Chem. Soc. 1967, 89, 5048; Breslow, R.; Haynie, R.; Mirra, J.; J. Am. Chem. Soc. 1959, 81, 247; Vol'pin, M. E.; Koreshkov, Yu. D.; Kursanov, D. N.; Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1959, 3, 560.
11. 2. Breslow, R.; Yuan, C.; J. Am. Chem. Soc. 1958, 80, 5991; Tobey. S. W.; West, R.; J. Am. Chem. Soc. 1964, 86, 1459; Breslow, R.; Altman, L. J.; Krebs, A.; Mohacsi, E.; Murata, I.; Peterson, R. A.: Posner. J., J. Am. Chem. Soc. 1965, 87, 1326; Farnum, D. G.; Mehta, G.; Silberman, R. G., J. Am. Chem. Soc. 1967, 89, 5048; Breslow, R.; Haynie, R.; Mirra, J.; J. Am. Chem. Soc. 1959, 81, 247; Vol'pin, M. E.; Koreshkov, Yu. D.; Kursanov, D. N.; Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1959, 3, 560.
12. 3. Breslow, R.; Eicher, T.; Krebs, A.; Peterson, R. A.; Posner, J.; J. Am. Chem. Soc. 1965, 87, 1320: Föhlisch, B.; Bürgle, P.; Tetrahedron Lett. 1965, 30, 2661; Yoshida, H.; Yagi, K.; Tamai, T.; Sono, H.: Ogata, T.; Matsumoto, K.; Bull. Chem. Soc. Jpn. 1985, 58, 1073.
13. 3. Breslow, R.; Eicher, T.; Krebs, A.; Peterson, R. A.; Posner, J.; J. Am. Chem. Soc. 1965, 87, 1320: Föhlisch, B.; Bürgle, P.; Tetrahedron Lett. 1965, 30, 2661; Yoshida, H.; Yagi, K.; Tamai, T.; Sono, H.: Ogata, T.; Matsumoto, K.; Bull. Chem. Soc. Jpn. 1985, 58, 1073.
14. 3. Breslow, R.; Eicher, T.; Krebs, A.; Peterson, R. A.; Posner, J.; J. Am. Chem. Soc. 1965, 87, 1320: Föhlisch, B.; Bürgle, P.; Tetrahedron Lett. 1965, 30, 2661; Yoshida, H.; Yagi, K.; Tamai, T.; Sono, H.: Ogata, T.; Matsumoto, K.; Bull. Chem. Soc. Jpn. 1985, 58, 1073.
15. 4. Stang, P. J.; Maas, G.; Smith, D. L.; McCloskey, J. A.; J. Am. Chem. Soc. 1981, 103, 4837.
16. 5. Gleiter, R.; Merger, M.; Tetrahedron Lett. 1992, 33, 3473.
17. 6. Gleiter, R.; Merger, M.; Oeser, T.; Irngartinger, H.; Tetrahedron Lett. 1995, 36, 6425.
18. 7. Gleiter, R.; Merger, M.; Altreuther, A.; Irngartinger, H.; J. Org. Chem. 1996, 61, 1946.
19. 8. Gleiter, R.; Merger, M.; Altreuther, A.; Irngartinger, H.; J. Org. Chem. 1995, 60, 4692
20. 2).
21. 2).
22. 2).
23. 12. Schuster, A.; Gleiter, R. to be published.
24. 3. The crystal structure has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 133120.
25. 14. Sheldrick, G. M. 1996, unpublished work, based on the method described in Blessing, R. H. Acta Crystallographica, Sect. A, 1995, 51, 33.
26. 15. Sheldrick, G. M.; Bruker Analytical X-ray Division, Madison, WI 1995.