Domino reactions of a double δ,ε-unsaturated dioxime: Competition between two intramolecular cycloaddition pathways

Synlett

Volumn , Issue 3, 1998, Pages 277-279

  Baskaran, Subramanian ^a   Aurich, Hans Günter ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 26844520896     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1623     Document Type: Article

References (19)

1. (a) Tufariello, J.J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley-interscience: New York, 1984, vol.2, chap.9, p.83;
2. (b) Breuer, E. In Nitrones, Nitronates & Nitroxides, Patai, S.; Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1989, pp. 180 and 260;
3. (c) Torsseil, K.B.G. Nitrite Oxides, Nitrones and Nitronates in Organic Synthesis: VCH Publishers, Inc: Weinheim 1988; p.20;
4. th ed. vol. E14b, Klamann, D.; Hagemann, H.; Eds.; Thieme: Stuttgart, 1990, p.1521.
5. Wade, P.A. In Comprehensive Organic Synthesis, Eds.; Trost, B.M.; Fleming, L; Semmelhack, M.F.; Pergamon, Oxford 1991, Vol 4, chap 4.10.2; see also ref. 1a p.116, ref. 1b pp.182, 264, ref 1c, p.194.
6. See ref. 1a p. 135; ref. 1b pp. 182, 264, ref. 1c p. 271; ref. 1d p. 1391.
7. Aurich, H.G.; Biesemeier, F. Synthesis 1995, 1171.
8. (a) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W.J. Tetrahedron 1992, 48, 6929;
9. (b) Grigg, R.; Markandu, J.; Surendrakumar, S.; Thornton-Pett, M.; Warnock, W.J. Tetrahedron 1992, 48, 10399.
10. Dioxime 3 was prepared in analogy to the procedure described before, see ref 4.
11. +, 100).
12. Since every step of the reaction sequence must take place twice, it is not surprising that the yield of cycloadducts formed via 3 should be relatively low.
13. (a) Aurich, H.G.; Biesemeier, F.; Geiger, M.; Harms, K. Liebigs Ann J Recueil, 1997, 423;
14. (b) Aurich, H.G.; Biesemeier, R; Harms, K. Liebigs Ann/Recueil, 1997, 469;
15. (c) Aurich, H.G.; Geiger, M.; Sievers, U. Synlett, 1997, 1004.
16. X-ray analysis was performed by Dr. K. Harms and will be published later.
17. Davidson, E.C.; Forbes, I.A.; Holmes, A.B.; Warner, J.A. Tetrahedron, 1996, 52, 11601.
18. O'Mahony, C.; Heaney, F.; J. Chem. Soc., Chem. Commun, 1996, 167.
19. Takeuchi, Y.; Furusaki, F.; In Advances in Heterocyclic Chemistry; Katrizky, A.R.; Boulton, A.J.; Eds.; Academic: New York, 1997, vol.21, pp 243-244.