Synthesis of [1.1.1]Propellanes by Cyclization of 3-Alkylidenecyclobutylidenes

Advanced Synthesis and Catalysis

Volumn 339, Issue 3, 1997, Pages 217-232

  Kenndoff, Monika ^a   Singer, Andrea ^b   Szeimies, Günter ^b  

^a UNIVERSITY OF MUNICH   (Germany)

^b HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2742566228     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. In part from M. Kenndoff, Dissertation, Univ. München 1992
2. K. B. Wiberg, F. H. Walker, J. Am. Chem. Soc. 104 (1982) 5239
3. a) K. Semmler, G. Szeimies, J. Belzner, J. Am. Chem. Soc. 107 (1985) 6410;
4. b) J. Belzner, U. Bunz, K. Semmler, G. Szeimies, K. Opitz, A.-D. Schlüter, Chem. Ber. 122 (1989) 397
5. J. Belzner, G. Szeimies, Tetrahedron Lett. 1987, 3099
6. G. Kottirsch, K. Polborn, G. Szeimies, J. Am. Chem. Soc. 110 (1988) 5588
7. J. Belzner, B. Gareiß, K. Polborn, W. Schmidt, K. Semmler, G. Szeimies, Chem. Ber. 122 (1989) 1509
8. M. Christi, G. Brüntrup, Chem. Ber. 87 (1974) 488
9. a) N. O. Nilsen, L. Skattebøl, Tetrahedron Lett. 1984, 2887;
10. b) A. Düker, Dissertat. Univ. München, 1986
11. G. Szeimies, F. Philipp, O. Baumgärtel, J. Harnisch, Tetrahedron Lett. 1977, 2135
12. a) K. B. Wiberg, J. E. Hiatt, G. J. Burgmaier, Tetrahedron Lett. 1968, 5855;
13. b) A. Greenberg, Tetrahedron Lett. 1978, 3509
14. E. J. Corey, C. U. Kim, M. Takeda, Tetrahedron Lett 1972, 4339
15. A. M. Orendt, J. C. Facelli, D. M. Grant, J. Michl, F. H. Walker, W. P. Dailey, S. T. Waddell, K. B. Wiberg, M. Schindler, W. Kutzelnigg, Theor. Chim. Acta 68 (1985) 421
16. J. Backes, U. H. Brinker, in Houben-Weyl, Methoden der Organischen Chemie, Vol. E19b (M. Regitz, ed.), Georg Thieme Verlag, Stuttgart 1989, pp 510
17. P. M. Warner, Chem. Rev. 89 (1989) 1067, and references given therein
18. U. H. Brinker, W. Erdle, Angew. Chem. 99 (1987) 1290; Angew. Chem. Int. Ed. Engl. 26 (1987) 1260
19. U. H. Brinker, W. Erdle, Angew. Chem. 99 (1987) 1290; Angew. Chem. Int. Ed. Engl. 26 (1987) 1260
20. Gaussian 94 (Revision B.3), M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. A. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, Gaussian, Inc. Pittsburgh PA, 1995
21. M. J. Frisch, A. Frisch, J. B. Foresman, Gaussian 94 User's Reference, Gaussian Inc. 1995, and references therein
22. T. Ziegler, Chem. Rev. 91 (1991) 651; J. Labanowski, J. Andzelm, Eds. Density Functional Methods in Chemistry, Springer, Berlin 1991
23. T. Ziegler, Chem. Rev. 91 (1991) 651; J. Labanowski, J. Andzelm, Eds. Density Functional Methods in Chemistry, Springer, Berlin 1991
24. C. J. Cramer, F. J. Dulles, J. W. Storer, S. E. Worthington, Chem. Phys. Lett. 218 (1994) 387
25. See for example: E. Goldstein, B. Beno, K. N. Houk, J. Am. Chem. Soc. 118 (1996) 6036. J. Cioslowski, Y. Liu, M. Martinov, P. Piskorz, D. Moncrieff, J. Am. Chem. Soc. 118 (1996) 5261
26. See for example: E. Goldstein, B. Beno, K. N. Houk, J. Am. Chem. Soc. 118 (1996) 6036. J. Cioslowski, Y. Liu, M. Martinov, P. Piskorz, D. Moncrieff, J. Am. Chem. Soc. 118 (1996) 5261
27. K. Rosendorfer, O. Jarosch, K. Polborn, G. Szeimies, Liebigs Ann. 1995, 1765
28. R. Otto, O. v. Gruber, Liebigs Ann. Chem. 142 (1897) 98
29. a) D. van Leusen, A. M. van Leusen, Synthesis 1980, 325;
30. b) M. Krumpolc, J. Rocek, Org. Synth, Coll. Vol. 7 (1990) 114
31. D. A. Bak, W. T. Brady, J. Org. Chem. 44 (1979) 107. 10k was obtained in 85% yield by reaction of 2,2-dichloro-3,3,4,4-tetramethylcyclobutanone with 4 equiv. of activated Zn in acetic acid for 15 h at 60°C.
32. L. Brandsma, Preparative Acetylenic Chemistry, Elsevier, Amsterdam 1988, p 24-25, 102-103, 167, 195
33. H. Gilman, F. K. Cartledge, J. Organomet. Chem. 2 (1964) 447