Thermolysis and photolysis of two steroidal hydroxamic acid methanesulfonates

Canadian Journal of Chemistry

Volumn 75, Issue 6, 1997, Pages 857-872

  Edwards, Oliver E ^a   Grue Sørensen, Gunnar ^b,c   Blackwell, Barbara A ^d  

^a CARLETON UNIVERSITY   (Canada)

^b LEO PHARMA A S   (Denmark)

^c NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^d OTTAWA RESEARCH AND DEVELOPMENT CENTRE   (Canada)

Author keywords

3 aza A norcholestanes; 4 aza A nor B homocholestanes; Aza Favorskii ring contraction.; Steroidal enamides

Indexed keywords

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PYROLYSIS; SULFUR COMPOUNDS; ULTRAVIOLET SPECTROSCOPY;

STEROIDS; THERMOLYSIS;

PHOTOLYSIS;

HYDROXAMIC ACID; MESYLIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PHOTOLYSIS; ULTRAVIOLET RADIATION;

EID: 0031170962     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v97-104     Document Type: Article

References (29)

1. (a) B.W. Bycroft. Nature, 224, 595 (1969); In Comprehensive organic chemistry. Vol. 5. Edited by D.H.R. Barton and W.D. Ollis. Pergamon Press, New York. 1979. pp. 241-287; U. Redeker, N. Engel, and W. Steglich. Tetrahedron Lett. 22 4263 (1981);
2. (a) B.W. Bycroft. Nature, 224, 595 (1969); In Comprehensive organic chemistry. Vol. 5. Edited by D.H.R. Barton and W.D. Ollis. Pergamon Press, New York. 1979. pp. 241-287; U. Redeker, N. Engel, and W. Steglich. Tetrahedron Lett. 22 4263 (1981);
3. (a) B.W. Bycroft. Nature, 224, 595 (1969); In Comprehensive organic chemistry. Vol. 5. Edited by D.H.R. Barton and W.D. Ollis. Pergamon Press, New York. 1979. pp. 241-287; U. Redeker, N. Engel, and W. Steglich. Tetrahedron Lett. 22 4263 (1981);
4. (b) O.E. Edwards and W. Rank. Can. J. Chem. 68, 1425 (1990), and references therein;
5. (c) O.E. Edwards, J.L. Douglas, D.C. Horwell, W. Rank, and T. Sano. Can.J. Chem. 70, 2405 (1992);
6. (d) T.G. Back and K. Brunner. J. Org. Chem. 54, 1904 (1989), and references therein;
7. (e) H. Hiemstra and W.N. Speckamp. In Comprehensive organic synthesis. Vol. 2. Edited by B.M. Frost. Pergamon Press, London. 1991. pp. 1046-1082;
8. O.E. Edwards, A.M. Greaves, and W.-W. Sy. Can. J. Chem. 66, 1163 (1988), and references therein.
9. W.A. Court, O.E. Edwards, C. Grieco, W. Rank, and T. Sano. Can. J. Chem. 53, 463 (1975).
10. (a) N.J. Doorenbos, C.L. Huang, C.R. Tamorria, and M.L. Wu. J. Org. Chem. 16, 2546 (1961);
11. (b) M. Uskaković and M. Gut. Helv. Chim. Acta, 42, 2258 (1959).
12. R.V. Hoffman and N.K. Nayyar. J. Org. Chem. 59, 3530 (1994); R.V. Hoffman, N.K. Nayyar, J.M. Shankweiler, and B.W. Klinekole III. Tetrahedron Lett. 35, 3231 (1994).
13. R.V. Hoffman and N.K. Nayyar. J. Org. Chem. 59, 3530 (1994); R.V. Hoffman, N.K. Nayyar, J.M. Shankweiler, and B.W. Klinekole III. Tetrahedron Lett. 35, 3231 (1994).
14. J.T. Edward and P.F. Morand. Can. J. Chem. 38, 1316 (1960).
15. G. Rosenkranz, O. Mancera, F. Sondheimer, and C. Djerassi. J. Org. Chem. 21, 520 (1956).
16. (a) C.M. Bladon and G.W. Kirby. J. Chem. Soc. Chem. Commun. 1402 (1982);
17. (b) J.C. Sheehan. Angew. Chem. Int. Ed. Engl. 8, 1 (1969);
18. (c) H.E. Baumgarten, R.D. Clark, L.S. Endres, L.D. Hagemeier, and V.J. Elia. Tetrahedron Lett. 5053 (1967).
19. O.E. Edwards and M. Lesage. Can. J. Chem. 41, 1594 (1963).
20. J.D.G. Cadogan and A.G. Rowley. J. Chem. Soc. Perkin Trans. 1, 1069 (1975).
21. (a) P.J. Kropp. Acc. Chem. Res. 17, 131 (1984); O.E. Edwards and P-T. Ho. Can. J. Chem. 56, 733 (1979); H.E. Zimmerman. Angew. Chem. Int. Ed. Engl. 8, 1 (1969); J.A. Pincock. Acc. Chem. Res. 30, 43 (1997);
22. (a) P.J. Kropp. Acc. Chem. Res. 17, 131 (1984); O.E. Edwards and P-T. Ho. Can. J. Chem. 56, 733 (1979); H.E. Zimmerman. Angew. Chem. Int. Ed. Engl. 8, 1 (1969); J.A. Pincock. Acc. Chem. Res. 30, 43 (1997);
23. (a) P.J. Kropp. Acc. Chem. Res. 17, 131 (1984); O.E. Edwards and P-T. Ho. Can. J. Chem. 56, 733 (1979); H.E. Zimmerman. Angew. Chem. Int. Ed. Engl. 8, 1 (1969); J.A. Pincock. Acc. Chem. Res. 30, 43 (1997);
24. (a) P.J. Kropp. Acc. Chem. Res. 17, 131 (1984); O.E. Edwards and P-T. Ho. Can. J. Chem. 56, 733 (1979); H.E. Zimmerman. Angew. Chem. Int. Ed. Engl. 8, 1 (1969); J.A. Pincock. Acc. Chem. Res. 30, 43 (1997);
25. (b) H. Vancik, V. Gabelica, V. Rogan, and D.E. Sunko. J. Chem. Res. (S), 92 (1990).
26. T.G. Back, J.H.-L. Chau, P.W. Codding, P.I. Gladstone, D.H. Jones, J.W. Morzycke, and A.W. Roszak. J. Org. Chem. 57, 4110 (1992).
27. J.B. Stothers. Carbon-13 NMR spectroscopy. Academic Press, New York. 1972. p. 427, and references therein.
28. R.B. Turner. J. Am. Chem. Soc. 72, 579 (1950).
29. H. Singh and D. Paul. J. Chem. Soc. Perkin Trans, 1, 1475 (1974).