Rearrangement of oxaspiroheptanes to cyclohexanones mediated by lithium iodide

Synlett

Volumn , Issue 5, 2000, Pages 749-751

  Bouyssi, Didier ^a   Cavicchioli, Marcello ^a   Large, Sylvie ^a   Monteiro, Nuno ^a   Balme, Geneviève ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

Cyclohexanones; Epoxides; Ring expansion

Indexed keywords

ALKANONE; CYCLOHEXANONE DERIVATIVE; HEPTANE; LITHIUM;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DECARBOXYLATION; REACTION ANALYSIS; TEMPERATURE;

EID: 0034072534     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

1. For review on ring expansions, see Hesse, M. Ring Enlargement in Organic Chemistry, VCH, New York 1991; Gutsche, C.D.; Redmore, D.; Carbocyclic Ring Expansion Reactions, Academic Press, New York 1968.
2. For review on ring expansions, see Hesse, M. Ring Enlargement in Organic Chemistry, VCH, New York 1991; Gutsche, C.D.; Redmore, D.; Carbocyclic Ring Expansion Reactions, Academic Press, New York 1968.
3. Leriverend, M.-L.; Leriverend, P. C. R. Acad. Sc. Paris, Série C 1975, 280, 791. Leriverend, M.-L.; Leriverend, P. Chem. Ber. 1976, 709, 3492. Trost, B.M.; Latimer, L.H. J. Org. Chem. 1978, 43, 1031. Morton, D.R.; Brokaw, F.C. J. Org. Chem. 1979, 44, 2880. Krief, A.; Halazy, S. J. Chem. Soc., Chem. Commun. 1982, 1200. Halazy, S.; Zutterman, F.; Krief, A. Tetrahedron Lett. 1982, 23, 4385. Newton, R.F.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. I 1982, 823. Leriverend, M.-L.; Vazeux, M. J. Chem. Soc., Chem. Commun. 1982, 866. Wenkert, E.; Arrhenius, T.S. J. Am. Chem. Soc. 1983, 705, 2030. Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. Hart, T.W.; Comte, M.-T. Tetrahedron Lett. 1985, 26, 2713. Pirrung, M. C.; Thomson, S.A. J. Org. Chem. 1988, 53, 227. Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron Lett. 1999, 40, 5183.
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5. Leriverend, M.-L.; Leriverend, P. C. R. Acad. Sc. Paris, Série C 1975, 280, 791. Leriverend, M.-L.; Leriverend, P. Chem. Ber. 1976, 709, 3492. Trost, B.M.; Latimer, L.H. J. Org. Chem. 1978, 43, 1031. Morton, D.R.; Brokaw, F.C. J. Org. Chem. 1979, 44, 2880. Krief, A.; Halazy, S. J. Chem. Soc., Chem. Commun. 1982, 1200. Halazy, S.; Zutterman, F.; Krief, A. Tetrahedron Lett. 1982, 23, 4385. Newton, R.F.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. I 1982, 823. Leriverend, M.-L.; Vazeux, M. J. Chem. Soc., Chem. Commun. 1982, 866. Wenkert, E.; Arrhenius, T.S. J. Am. Chem. Soc. 1983, 705, 2030. Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. Hart, T.W.; Comte, M.-T. Tetrahedron Lett. 1985, 26, 2713. Pirrung, M. C.; Thomson, S.A. J. Org. Chem. 1988, 53, 227. Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron Lett. 1999, 40, 5183.
6. Leriverend, M.-L.; Leriverend, P. C. R. Acad. Sc. Paris, Série C 1975, 280, 791. Leriverend, M.-L.; Leriverend, P. Chem. Ber. 1976, 709, 3492. Trost, B.M.; Latimer, L.H. J. Org. Chem. 1978, 43, 1031. Morton, D.R.; Brokaw, F.C. J. Org. Chem. 1979, 44, 2880. Krief, A.; Halazy, S. J. Chem. Soc., Chem. Commun. 1982, 1200. Halazy, S.; Zutterman, F.; Krief, A. Tetrahedron Lett. 1982, 23, 4385. Newton, R.F.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. I 1982, 823. Leriverend, M.-L.; Vazeux, M. J. Chem. Soc., Chem. Commun. 1982, 866. Wenkert, E.; Arrhenius, T.S. J. Am. Chem. Soc. 1983, 705, 2030. Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. Hart, T.W.; Comte, M.-T. Tetrahedron Lett. 1985, 26, 2713. Pirrung, M. C.; Thomson, S.A. J. Org. Chem. 1988, 53, 227. Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron Lett. 1999, 40, 5183.
7. Leriverend, M.-L.; Leriverend, P. C. R. Acad. Sc. Paris, Série C 1975, 280, 791. Leriverend, M.-L.; Leriverend, P. Chem. Ber. 1976, 709, 3492. Trost, B.M.; Latimer, L.H. J. Org. Chem. 1978, 43, 1031. Morton, D.R.; Brokaw, F.C. J. Org. Chem. 1979, 44, 2880. Krief, A.; Halazy, S. J. Chem. Soc., Chem. Commun. 1982, 1200. Halazy, S.; Zutterman, F.; Krief, A. Tetrahedron Lett. 1982, 23, 4385. Newton, R.F.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. I 1982, 823. Leriverend, M.-L.; Vazeux, M. J. Chem. Soc., Chem. Commun. 1982, 866. Wenkert, E.; Arrhenius, T.S. J. Am. Chem. Soc. 1983, 705, 2030. Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. Hart, T.W.; Comte, M.-T. Tetrahedron Lett. 1985, 26, 2713. Pirrung, M. C.; Thomson, S.A. J. Org. Chem. 1988, 53, 227. Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron Lett. 1999, 40, 5183.
8. Leriverend, M.-L.; Leriverend, P. C. R. Acad. Sc. Paris, Série C 1975, 280, 791. Leriverend, M.-L.; Leriverend, P. Chem. Ber. 1976, 709, 3492. Trost, B.M.; Latimer, L.H. J. Org. Chem. 1978, 43, 1031. Morton, D.R.; Brokaw, F.C. J. Org. Chem. 1979, 44, 2880. Krief, A.; Halazy, S. J. Chem. Soc., Chem. Commun. 1982, 1200. Halazy, S.; Zutterman, F.; Krief, A. Tetrahedron Lett. 1982, 23, 4385. Newton, R.F.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. I 1982, 823. Leriverend, M.-L.; Vazeux, M. J. Chem. Soc., Chem. Commun. 1982, 866. Wenkert, E.; Arrhenius, T.S. J. Am. Chem. Soc. 1983, 705, 2030. Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. Hart, T.W.; Comte, M.-T. Tetrahedron Lett. 1985, 26, 2713. Pirrung, M. C.; Thomson, S.A. J. Org. Chem. 1988, 53, 227. Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron Lett. 1999, 40, 5183.
9. Leriverend, M.-L.; Leriverend, P. C. R. Acad. Sc. Paris, Série C 1975, 280, 791. Leriverend, M.-L.; Leriverend, P. Chem. Ber. 1976, 709, 3492. Trost, B.M.; Latimer, L.H. J. Org. Chem. 1978, 43, 1031. Morton, D.R.; Brokaw, F.C. J. Org. Chem. 1979, 44, 2880. Krief, A.; Halazy, S. J. Chem. Soc., Chem. Commun. 1982, 1200. Halazy, S.; Zutterman, F.; Krief, A. Tetrahedron Lett. 1982, 23, 4385. Newton, R.F.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. I 1982, 823. Leriverend, M.-L.; Vazeux, M. J. Chem. Soc., Chem. Commun. 1982, 866. Wenkert, E.; Arrhenius, T.S. J. Am. Chem. Soc. 1983, 705, 2030. Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. Hart, T.W.; Comte, M.-T. Tetrahedron Lett. 1985, 26, 2713. Pirrung, M. C.; Thomson, S.A. J. Org. Chem. 1988, 53, 227. Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron Lett. 1999, 40, 5183.
10. Leriverend, M.-L.; Leriverend, P. C. R. Acad. Sc. Paris, Série C 1975, 280, 791. Leriverend, M.-L.; Leriverend, P. Chem. Ber. 1976, 709, 3492. Trost, B.M.; Latimer, L.H. J. Org. Chem. 1978, 43, 1031. Morton, D.R.; Brokaw, F.C. J. Org. Chem. 1979, 44, 2880. Krief, A.; Halazy, S. J. Chem. Soc., Chem. Commun. 1982, 1200. Halazy, S.; Zutterman, F.; Krief, A. Tetrahedron Lett. 1982, 23, 4385. Newton, R.F.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. I 1982, 823. Leriverend, M.-L.; Vazeux, M. J. Chem. Soc., Chem. Commun. 1982, 866. Wenkert, E.; Arrhenius, T.S. J. Am. Chem. Soc. 1983, 705, 2030. Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. Hart, T.W.; Comte, M.-T. Tetrahedron Lett. 1985, 26, 2713. Pirrung, M. C.; Thomson, S.A. J. Org. Chem. 1988, 53, 227. Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron Lett. 1999, 40, 5183.
11. Leriverend, M.-L.; Leriverend, P. C. R. Acad. Sc. Paris, Série C 1975, 280, 791. Leriverend, M.-L.; Leriverend, P. Chem. Ber. 1976, 709, 3492. Trost, B.M.; Latimer, L.H. J. Org. Chem. 1978, 43, 1031. Morton, D.R.; Brokaw, F.C. J. Org. Chem. 1979, 44, 2880. Krief, A.; Halazy, S. J. Chem. Soc., Chem. Commun. 1982, 1200. Halazy, S.; Zutterman, F.; Krief, A. Tetrahedron Lett. 1982, 23, 4385. Newton, R.F.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. I 1982, 823. Leriverend, M.-L.; Vazeux, M. J. Chem. Soc., Chem. Commun. 1982, 866. Wenkert, E.; Arrhenius, T.S. J. Am. Chem. Soc. 1983, 705, 2030. Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. Hart, T.W.; Comte, M.-T. Tetrahedron Lett. 1985, 26, 2713. Pirrung, M. C.; Thomson, S.A. J. Org. Chem. 1988, 53, 227. Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron Lett. 1999, 40, 5183.
12. Leriverend, M.-L.; Leriverend, P. C. R. Acad. Sc. Paris, Série C 1975, 280, 791. Leriverend, M.-L.; Leriverend, P. Chem. Ber. 1976, 709, 3492. Trost, B.M.; Latimer, L.H. J. Org. Chem. 1978, 43, 1031. Morton, D.R.; Brokaw, F.C. J. Org. Chem. 1979, 44, 2880. Krief, A.; Halazy, S. J. Chem. Soc., Chem. Commun. 1982, 1200. Halazy, S.; Zutterman, F.; Krief, A. Tetrahedron Lett. 1982, 23, 4385. Newton, R.F.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. I 1982, 823. Leriverend, M.-L.; Vazeux, M. J. Chem. Soc., Chem. Commun. 1982, 866. Wenkert, E.; Arrhenius, T.S. J. Am. Chem. Soc. 1983, 705, 2030. Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. Hart, T.W.; Comte, M.-T. Tetrahedron Lett. 1985, 26, 2713. Pirrung, M. C.; Thomson, S.A. J. Org. Chem. 1988, 53, 227. Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron Lett. 1999, 40, 5183.
13. Leriverend, M.-L.; Leriverend, P. C. R. Acad. Sc. Paris, Série C 1975, 280, 791. Leriverend, M.-L.; Leriverend, P. Chem. Ber. 1976, 709, 3492. Trost, B.M.; Latimer, L.H. J. Org. Chem. 1978, 43, 1031. Morton, D.R.; Brokaw, F.C. J. Org. Chem. 1979, 44, 2880. Krief, A.; Halazy, S. J. Chem. Soc., Chem. Commun. 1982, 1200. Halazy, S.; Zutterman, F.; Krief, A. Tetrahedron Lett. 1982, 23, 4385. Newton, R.F.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. I 1982, 823. Leriverend, M.-L.; Vazeux, M. J. Chem. Soc., Chem. Commun. 1982, 866. Wenkert, E.; Arrhenius, T.S. J. Am. Chem. Soc. 1983, 705, 2030. Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. Hart, T.W.; Comte, M.-T. Tetrahedron Lett. 1985, 26, 2713. Pirrung, M. C.; Thomson, S.A. J. Org. Chem. 1988, 53, 227. Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron Lett. 1999, 40, 5183.
14. Leriverend, M.-L.; Leriverend, P. C. R. Acad. Sc. Paris, Série C 1975, 280, 791. Leriverend, M.-L.; Leriverend, P. Chem. Ber. 1976, 709, 3492. Trost, B.M.; Latimer, L.H. J. Org. Chem. 1978, 43, 1031. Morton, D.R.; Brokaw, F.C. J. Org. Chem. 1979, 44, 2880. Krief, A.; Halazy, S. J. Chem. Soc., Chem. Commun. 1982, 1200. Halazy, S.; Zutterman, F.; Krief, A. Tetrahedron Lett. 1982, 23, 4385. Newton, R.F.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. I 1982, 823. Leriverend, M.-L.; Vazeux, M. J. Chem. Soc., Chem. Commun. 1982, 866. Wenkert, E.; Arrhenius, T.S. J. Am. Chem. Soc. 1983, 705, 2030. Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. Hart, T.W.; Comte, M.-T. Tetrahedron Lett. 1985, 26, 2713. Pirrung, M. C.; Thomson, S.A. J. Org. Chem. 1988, 53, 227. Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron Lett. 1999, 40, 5183.
15. Leriverend, M.-L.; Leriverend, P. C. R. Acad. Sc. Paris, Série C 1975, 280, 791. Leriverend, M.-L.; Leriverend, P. Chem. Ber. 1976, 709, 3492. Trost, B.M.; Latimer, L.H. J. Org. Chem. 1978, 43, 1031. Morton, D.R.; Brokaw, F.C. J. Org. Chem. 1979, 44, 2880. Krief, A.; Halazy, S. J. Chem. Soc., Chem. Commun. 1982, 1200. Halazy, S.; Zutterman, F.; Krief, A. Tetrahedron Lett. 1982, 23, 4385. Newton, R.F.; Wadsworth, A. H. J. Chem. Soc., Perkin Trans. I 1982, 823. Leriverend, M.-L.; Vazeux, M. J. Chem. Soc., Chem. Commun. 1982, 866. Wenkert, E.; Arrhenius, T.S. J. Am. Chem. Soc. 1983, 705, 2030. Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898. Hart, T.W.; Comte, M.-T. Tetrahedron Lett. 1985, 26, 2713. Pirrung, M. C.; Thomson, S.A. J. Org. Chem. 1988, 53, 227. Mahuteau-Betzer, F.; Ghosez, L. Tetrahedron Lett. 1999, 40, 5183.
16. Krapcho, A.P. Synthesis 1982, 805.
17. a) For the synthesis of 1a-1d see: Bouyssi, D.; Monteiro, N.; Balme, G. Tetrahedron Lett. 1999, 40, 1297.
18. b) for the synthesis of 1e, see Monteiro, N.; Balme, G.; Gore, J. Synlett 1992, 227.
19. 2 (2 ml). The resulting mixture was stirred at room temperature for 1 hour, then concentrated at reduced pressure. The residue was purified by flash chromatography on silica gel using petroleum ether and ether (1:1) as the eluent to give pure 3 (205 mg, 96%).
20. All new compounds gave satisfactory spectroscopic data.
21. Campbell, E.; Martin, J.J.; Bordner, J.; Kleinman, E.F. J. Org. Chem. 1995, 61, 4806.
22. Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1991, 47, 6293.