Facile Preparation of 3, 7-Diazabicyclo[3.3.0]octane and 3, 7, 10-Triheterocyclic [3.3.3]Propellane Ring Systems from 1, 5-Diazacyclooctane 3, 7-Derivatives

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8897-8903

  Dave, Paritosh R ^a,b   Forohar, Farhad ^a   Axenrod, Theodore ^a   Das, Kajal K ^a   Qi, Lida ^a   Watnick, Clara ^a   Yazdekhasti, Hamid ^a  

^a SCIENCE APPLICATIONS INTERNATIONAL CORPORATION   (United States)

^b CITY COLLEGE OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000118076     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9614755     Document Type: Article

References (25)

1. For a preliminary communication see: Dave, P. R.; Forohar, F. F.; Axenrod, T.; Qi, L.; Watnick, C.; Yazdekhasti, H. Tetrahedron Lett. 1994, 35, 8965.
2. Axenrod, T.; Watnick, C.; Yazdekhasti, H.; Dave, P. R. Tetrahedron Lett. 1993, 34, 6677.
3. For a review see Perlmutter, H. D. Adv. Heterocyd. Chem. 1989, 46, 1.
4. Cichra, D. A.; Adolph, H. G. Synthesis 1983, 830.
5. Li-Hua, X.; Ming-xuan, W.; En-pu, W.; Hui-min, T.; BØ-ren, C. Propellants, Explos., Pyrotech. 1988, 13, 21.
6. For a discussion of the use of this trivial nomenclature, see Knowles, P.; Harris, N. V. J. Chem. Soc., Perkin Trans, l 1983, 1475.
7. Altman, J.; Babad, E.; Itzchaki, J. Ginsburg, D. Tetrahedron, Suppl. 8, Part I, 1966, 279.
8. Schulze, K.; Winkler, G.; Dietrich, W.; Mühlstädt, M. Prakt. Chem. 1977, 319, 463.
9. Schulze, K.; Vetter, A.; Dietrich, W.; Mühlstädt, M. Z. Chem. 1977, 17, 174.
10. Lukin, S. S.; Levashova, V. I.; Bunina-Krivorukova, L. I.; Zlotskii, S. S. J. Org. Chem. USSR 1989, 2210.
11. Suzuki, M.; Lim, J.-C., Oguni, M.; Eberhardt, M.; Saegusa, T. Polym. J. 1990, 22, 815.
12. Paudler, W. W.; Gapski, G. R.; Barton, J. M. J. Org. Chem. 1966, 31, 277.
13. Bishop, R. J. Chem. Soc. Perkin Trans, l 1974, 2364.
14. A mixture of acetic acid and 6 N hydrochloric acid has successfully been used to remove the W-tosyl groups in 3, 7-disubstituted octahydrodiazocines over a four-week period; sec for example, reference 16.
15. Gold, E. H.; Babad. E. J. Org. Chem. 1972, 37, 2208.
16. See for example, Ganem, B.; Osby, J. O. Chem. Rev. 1986, 86, 763 and references cited therein.
17. Paudler, W. W.; Zeiler, A. G.; Gapski, G. R. J. Org. Chem. 1969, 34, 1001.
18. Camps, P.; Munoz-Torrero, D. Tetrahedron Lett. 1994, 35, 3187;
19. See also, Chapman, R. D.; Archibald, T. G.; Baum, K. Report No. ONR7-1 (Interim), 1989; Fluorochem Inc., Azusa, CA; AD-A214106; available from the National Technical Information Service, U.S. Department of Commerce, Springfield, VA 22161.
20. Waykole, L. M.; Shen, C. C.; Paquette, L. A. J. Org. Chem. 1988, 53, 4969.
21. Camps, P.; Munoz-Torrero, D., Munoz-Torrero, V. Tetrahedron Lett. 1995, 36, 1917.
22. Camps, P.; Font-Bardia, M.; Munoz-Torrero, D.; Solans, X. Liebigs Ann. Chem.. 1995, 523.
23. Ammon, H. L.; Zuyue, D.; Gilardi, R.; Dave, P. R.; Forohar, F.; Axenrod, T. Acta Crystallogr. Sect. B 1996, 52, 352.
24. Wu, Y.; Ahlberg, P. Acta Chem. Scand. 1992, 46, 60.
25. Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy; VCH Publishers: New York, 1987; p 277.