Magnetic shielding effect of amine and ammonium groups obtained from proton chemical shifts of androstane derivatives

Tetrahedron Letters

Volumn 44, Issue 32, 2003, Pages 5975-5978

  Iwamoto, Hajime ^a   Kondo, Yoshiaki ^a   Kawatani, Takefumi ^a   Haino, Takeharu ^a   Fukazawa, Yoshimasa ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 AZA 5ALPHA ANDROSTANONE; 4 AZA 5BETA ANDROSTANONE; AMINE; AMMONIUM DERIVATIVE; ANDROSTANE DERIVATIVE; PROTON; UNCLASSIFIED DRUG;

ANISOTROPY; ARTICLE; CHEMICAL BOND; CORRELATION COEFFICIENT; ELECTRIC FIELD; MAGNETISM; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0038644247     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01486-2     Document Type: Article

References (42)

1. Karplus M. J. Chem. Phys. 30:1959;11-15.
2. Garbisch E.W. Jr. J. Am. Chem. Soc. 86:1964;5561-5564.
3. Sternhell S. Quarterly Rev. 23:1969;236-270.
4. Haasnoot C.A.G., de Leeuw F.A.A.M., Altona C. Tetrahedron. 36:1980;2783-2792.
5. Jaime C., Osawa E., Takeuchi Y., Camps P. J. Org. Chem. 48:1983;4514-4519.
6. Corey E.J., Ponder J.W. Tetrahedron Lett. 25:1984;4325-4328.
7. Masamune S., Ma P., Moore R.E., Fujiyoshi T., Jaime C., Osawa E. J. Chem. Soc., Chem. Commun. 1986;261-263.
8. Anet F.A.L., Bourn A.J.R. J. Am. Chem. Soc. 87:1965;5250-5251.
9. Bell R.A., Saunders J.K. Can. J. Chem. 48:1970;1114-1122.
10. Hall L.D., Sanders J.K.M. J. Am. Chem. Soc. 102:1980;5703-5711.
11. Scheek R.M., Russo N., Boelens R., Kaptein R., van Boom J.H. J. Am. Chem. Soc. 105:1983;2914-2916.
12. Neuhaus D., Sheppard R.N., Bick I.R.C. J. Am. Chem. Soc. 105:1983;5996-6002.
13. Fukazawa Y., Deyama K., Usui S. Tetrahedron Lett. 33:1992;5803-5806.
14. Haino T., Yanase M., Fukazawa Y. Angew. Chem., Int. Ed. 37:1998;997-998.
15. Iwamoto H., Kawatani T., Fukazawa Y. Tetrahedron Lett. 42:2001;1551-1553.
16. Iwamoto H., Hirakata M., Usui S., Haino T., Fukazawa Y. Tetrahedron Lett. 43:2002;85-87.
17. Pople J.A. J. Chem. Phys. 24:1956;1111 Bovey, F. A. Nuclear Magnetic Resonance Spectroscopy; Academic Press: New York, 1969; pp. 64-71, 265-274.
18. Wilcox C.F. Jr., Farley E.N. J. Am. Chem. Soc. 106:1984;7195-7200.
19. Wilcox C.F. Jr., Weber K.A. J. Org. Chem. 51:1986;1088-1094.
20. Gust D., Moore T.A., Liddell P.A., Nemeth G.A., Makings L.R., Moore A.L., Barrett D., Pessiki P.J., Bensasson R.V., Rougee M., Chachaty C., de Schryver F.C., Van der Auweraer M., Holzwarth A.R., Connolly J.S. J. Am. Chem. Soc. 109:1987;846-856.
21. Fukazawa Y., Ogata K., Usui S. J. Am. Chem. Soc. 110:1988;8692-8693.
22. Yang Y., Haino T., Usui S., Fukazawa Y. Tetrahedron. 52:1996;2325-2336.
23. Fukazawa Y., Yang Y., Hayashibara T., Usui S. Tetrahedron. 52:1996;2847-2862.
24. Fukazawa Y., Haino T., Kondoh Y. Tetrahedron Lett. 40:1999;3591-3594.
25. Okajima T., Wang Z.-H., Fukazawa Y. Tetrahedron Lett. 30:1989;1551-1554.
26. Okajima T., Wang Z.-H., Fukazawa Y. Chem. Lett. 1991;37-40.
27. Wang Z.-H., Usui S., Fukazawa Y. Bull. Chem. Soc. Jpn. 66:1993;1239-1243.
28. Fukazawa Y., Usui S., Tanimoto K., Hirai Y. J. Am. Chem. Soc. 116:1994;8169-8175.
29. Fukazawa Y., Hayashibara T., Yang Y., Usui S. Tetrahedron Lett. 36:1995;3349-3352.
30. Iwamoto H., Yang Y., Usui S., Fukazawa Y. Tetrahedron Lett. 42:2001;49-51.
31. Turner R.B. J. Am. Chem. Soc. 72:1950;579-585.
32. Fujimoto G.I. J. Am. Chem. Soc. 73:1951;1856.
33. Griffith W.P., Ley S.V. Aldrichimica Acta. 23:1990;13-19.
34. 2=0.1176. Supplementary crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC 210952 for 1α and No. CCDC 210971 for 1β . Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
35. Buckingham A.D. Can. J. Chem. 38:1960;300-307.
36. McConnell H.M. J. Chem. Phys. 27:1957;226-229.
37. -8.
38. -8.
39. Sudmeier J.L., Reilley C.N. Anal. Chem. 36:1964;1698-1706.
40. Sudmeier J.L., Reilley C.N. Anal. Chem. 36:1964;1707-1712.
41. o|. The structures were solved by the direct method (Sir 92). Full-matrix least squares refinements converged to a conventional R factor of 0.047, wR=0.058. Crystallographic results have been deposited with the Cambridge Crystallographic Data Centre, UK as supplementary publication number CCDC No. 210972.
42. -8.