Dehydroquadricyclanes

Advanced Synthesis and Catalysis

Volumn 340, Issue 1, 1998, Pages 11-19

  Szeimies, Günter ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2742558848     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (25)

1. For nomenclature, see [2], footnote 2
2. J. Harnisch, O. Baumgärtel, G. Szeimies, M. Van sc-Meerssche, G. Germain, J.-P. Declercq, J. Am. Chem. Soc. 101 (1979) 3370
3. H. K. Hall Jr., C. D. Smith, J. H. Baldt, J. Am. Chem. Soc. 95 (1973) 3197
4. C. D. Smith, Org. Synth., Coll. Vol. VI, p. 962
5. For a review on this subject, see: J. F. Liebman, A. Greenberg, Chem. Rev. 89 (1989) 1225
6. R. J. Card, D. C. Neckers, J. Org. Chem. 43 (1978) 2958; T. Arai, T. Oguchi, T. Wakabayashi, M. Tsuchiya, Y. Nishimura, S. Oishi, H. Sakuragi, K. Tokumaru, Bull.Chem. Soc. Jpn. 60 (1987) 2937
7. R. J. Card, D. C. Neckers, J. Org. Chem. 43 (1978) 2958; T. Arai, T. Oguchi, T. Wakabayashi, M. Tsuchiya, Y. Nishimura, S. Oishi, H. Sakuragi, K. Tokumaru, Bull.Chem. Soc. Jpn. 60 (1987) 2937
8. For a short early overview, see: G. Szeimies, in Advances in Strain in Organic Chemistry, Vol. 2, B. Halton Ed., Jai Press Ltd., London 1992, p. 1
9. Gaussian 90, Revision F, M. J. Frisch, M. Head-Gordon, G. W. Trucks, J. B. Foresman, H. B. Schlegel, K. Raghavachari, M. Robb, J. S. Binkley, C. Gonzalez, D. J. Defrees, D. F. Fox, R. A. Whitesides, R. Seeger, C. F. Melius, J. Baker, R. L. Martin, L. R. Kahn, J. J. P. Stewart, S. Topiol, J. A. Pople. Gaussian Inc., Pittsburgh PA, 1990
10. Gaussian 94, Revision D.3, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. 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.
11. For TCSCF calculations on dehydroquadricyclanes, see J. Podlech, K. Polborn, G. Szeimies, J. Org. Chem. 58 (1993) 4113
12. J. B. Foresman, Aeleen Frisch, Exploring Chemistry with Electronic Structure Methods, 2nd ed., Gaussian, Inc., Pittsburgh, 1996, p. 64
13. O. Baumgärtel, G. Szeimies, Chem. Ber. 116 (1983) 2180
14. The gas phase acidity of quadricyclane 1 has been recently determined: H S. Lee, H. DePuy, V. M. Bierbaum, J. Am. Chem. Soc. 118 (1996) 5068. The findings of the authors that acidity at C-1 and C-2 are very similar, is not true for metalation of 1 in solution.
15. O. Baumgärtel, J. Harnisch, G. Szeimies, M. Van Meerssche, G. Germain, J.-P. Declercq, Chem. Ber. 116 (1983) 2205
16. J. Kenndoff, Dissertation, University of Munich, 1990
17. J. R. Wiseman, W. H. Pletcher, J. Am. Chem. Soc. 92 (1970) 7136
18. M. Stähle, R. Lehmann, J. Kramar, M. Schlosser, Chimia 39 (1985) 229
19. H. D. Verkruijsse, L. Brandsma, Recl. Trav. Chim. Pays-Bas 105 (1986) 66
20. J. Kenndoff, K. Polborn, G. Szeimies, J. Am. Chem. Soc. 112 (1990) 6117
21. S. Glück-Walther, Dissertation University of Munich, 1993
22. G. W. Klumpp, Recl. Trav. Chim. Pays-Bas 105 (1986) 1, and references therein
23. U. Heywang, G. Szeimies, Chem. Ber. 123 (1990) 121
24. J. Podlech, Dissertation University of Munich, 1993
25. R. Gleiter, F. Ohlbach, J. Org. Chem. 61 (1996) 4929