Effects of CNN Bond Angle Restriction in 2,3-Diazabicyclo[2.1.1]hexane Derivatives on Nitrogen Inversion Barrier, Ease of Oxidation, and Acidity

Journal of Organic Chemistry

Volumn 56, Issue 2, 1991, Pages 613-618

  Nelsen, Stephen F ^a   Petillo, Peter A ^a   Chang, Hao ^a   Frigo, Timothy B ^a   Dougherty, Dennis A ^b   Kaftory, Menahem ^c  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^c TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001289866     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00002a024     Document Type: Article

References (28)

1. Chang, M. H.; Jain, R.; Dougherty, D. A. J. Am. Chem. Soc. 1984, 106, 4211.
2. Anet, F. A. L.; Osyany, J. M. J. Am. Chem. Soc. 1967, 89, 352.
3. Boggs, G. R.; Gerig, T. J. J. Org. Chem. 1969, 34, 1489.
4. Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1977, 99, 4889, 4907.
5. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
6. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221.
7. Agmon, I.; Kaftory, M.; Nelsen, S. F.; Blackstock, S. C. J. Am. Chem. Soc. 1986, 108, 4477.
8. Krow, G. R.; Lee, Y. B.; Szczapanski, S. W.; Zacharias, D. E.; Bailey, D. B. J. Am. Chem. Soc. 1987, 109, 5744.
9. Nelsen, S. F.; Frigo, T. B.; Kim, Y. J. Am. Chem. Soc. 1989, 111, 5387.
10. Nelsen, S. F.; Blackstock, S. C.; Rumack, D. T. J. Am. Chem. Soc. 1983, 105, 3115.
11. Brogli, F.; Eberbach, W.; Haselbach, E.; Heilbronner, E.; Hornung, V.; Lemal, D. M. Helv. Chim. Acta 1973, 56, 1933.
12. Schmidt, H.; Schweig, A.; Trost, B. M.; Neubold, H. B.; Scudder, P. H. J. Am. Chem. Soc. 1974, 96, 622.
13. Boyd, R. J.; Bünzli, J. C.; Snyder, J. P.; Heyman, M. L. J. Am. Chem. Soc. 1973, 95, 6478.
14. Rieber, N.; Alberts, J.; Lipsky, J. A.; Lemal, D. M. J. Am. Chem. Soc. 1969, 91, 5668.
15. Nelsen, S. F.; Blackstock, S. C.; Frigo, T. B. Tetrahedron 1986, 42, 1769.
16. Bunnett, J. F.; Olsen, F. P. Can. J. Chem. 1966, 44, 1899, 1917.
17. Kao, J.; Huang, T.-N. J. Am. Chem. Soc. 1979, 101, 5546.
18. Kao, J.; Leister, D. J. Am. Chem. Soc. 1988, 110, 7286.
19. Engel, P. S. J. Am. Chem. Soc. 1976, 98, 1972.
20. Kruger, P. J. The Chemistry of the Hydrazo, Azo, and Azoxy Groups; Patai, S., Ed.; J. Wiley and Sons; New York, 1975; Part 1, p 167.
21. Still, C. W.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 443, 2923.
22. Cookson, R. C.; Gupte, S. S.; Stevens, I. D. R.; Watts, C. T. Org. Synth. 1971, 51, 121.
23. Mintz, M. J.; Walling, C. Org. Synth. Wiley: New York, 1963; Collect. Vol. 4, p 184.
24. Nelaen, S. F.; Gannett, P. M. J. Am. Chem. Soc. 1982, 104, 5292.
25. Nelsen, S. F.; Weisman, G. R. J. Am. Chem. Soc. 1976, 98, 1842.
26. Main, P.; Fiske, S. J.; Hull, S. K.; Lessinger, L.; Germain, G.; Declerq, S. P.; Woolfson, M. M. MULTAN 80, A System of Computer Programs for the Automatic Solution of Crystal Structures from X-Ray Diffraction Data, Universités of York, England, and Louvain, Belgium.
27. Sheldrick, G. M. SHELX, Program for Crystal Structure Determination, Cambridge University, 1976.
28. Nelsen, S. F.; Rumack, D. T.; Meot-Ner Mautner, M. J. Am. Chem. Soc. 1988, 110, 7945.