Syntheses of selectively fluorinated cyclodecenones: The first deployment of the neutral oxy-Cope rearrangement in organofluorine chemistry

Organic and Biomolecular Chemistry

Volumn 1, Issue 24, 2003, Pages 4423-4434

  DiMartino, Gianluca ^a   Hursthouse, Michael B ^b   Light, Mark E ^b   Percy, Jonathan M ^c   Spencer, Neil S ^a   Tolley, Malcolm ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^c UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; ALKALINITY; CARBONYLATION; COLUMN CHROMATOGRAPHY; FLUORINE COMPOUNDS; ISOMERIZATION; MICROANALYSIS; NEGATIVE IONS; OLEFINS; PURIFICATION; SYNTHESIS (CHEMICAL); THERMOANALYSIS; X RAY CRYSTALLOGRAPHY;

DIFLUORINATION; PROTONATION;

KETONES;

OXY;

EPOXIDE; FLUORINATED HYDROCARBON; FLUORINE; HETEROCYCLIC COMPOUND;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; EPOXY COMPOUNDS; FLUORINE; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, FLUORINATED; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 0347537923     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b311261f     Document Type: Article

References (48)

1. J. A. Berson and M. Jones, J. Am. Chem. Soc., 1964, 86, 5019-5020.
2. For an extensive review of oxy-Cope and related rearrangements, see: H. Frauenrath, in Stereoselective Synthesis, ed. G. Helmchen, R. W. Hoffmann, J. Mulzer, and E. Schaumann, Stuttgart, 1996, vol. 6, pp. 3547-3688.
3. P. Heimbach, Angew. Chem., Int. Ed. Engl., 1964, 3, 702-703.
4. D. L. J. Clive, P. W. M. Sgarbi, X. He, S. Y. Sun, J. H. Zhang and L. G. Ou, Can. J. Chem., 2003, 81, 811-824.
5. D. A. Evans and A. M. Golob, J. Am. Chem. Soc., 1975, 97, 4765-4766.
6. L. A. Paquette, Tetrahedron, 1997, 53, 13971-14020.
7. L. Gentric, I. Hanna and L. Ricard, Org. Lett., 2003, 5, 1139-1142.
8. J. M. Yu, T. Wang, X. Y. Z. Wearing, J. Ma and J. M. Cook, J. Org. Chem., 2003, 68, 5852-5859.
9. L. A. Paquette, R. Guevel, S. Sakamoto, I. H. Kim and J. Crawford, J. Org. Chem., 2003, 68, 6096-6107.
10. J. Yang, Y. O. Long and L. A. Paquette, J. Am. Chem. Soc., 2003, 125, 1567-1574.
11. H. Miyaoka, T. Baba, H. Mitome and Y. Yamada, Tetrahedron Lett., 2001, 42, 9233-9236.
12. J. T. Njardarson and J. L. Wood, Org. Lett., 2001, 3, 2431-2434.
13. W. R. Dolbier, A. C. Alty and O. Phanstiel, J. Am. Chem. Soc., 1987, 109, 3046-3050.
14. W. E. Doering, V. G. Toscano and G. H. Beasley, Tetrahedron, 1971, 27, 5299-5306.
15. S. Y. Wang and W. T. Borden, J. Am. Chem. Soc., 1989, 111, 7282-7283.
16. K. J. Shea and R. B. Phillips, J. Am. Chem. Soc., 1980, 102, 3156-3162.
17. W. R. Dolbier and K. W. Palmer, J. Am. Chem. Soc., 1993, 115, 9349-9350.
18. W. R. Dolbier, K. W. Palmer, F. Tian, P. Fiedorow, A. Zaganiaczyk and H. Koroniak, Collect. Czech. Chem. Commun., 2002, 67, 1517-1532.
19. F. Haeffner, K. N. Houk, S. M. Schulze and J. K. Lee, J. Org. Chem., 2003, 68, 2310-2316 describes recent treatments of anionic sigmatropic rearrangements using DFT methods in which biradical pathways appear significant. For an experimental observation of biradical character in the Cope rearrangement of a perhalogenated hexadiene, see: N. Y. Jing and D. M. Lemal, J. Am. Chem. Soc., 1993, 115, 8481-8482.
20. F. Haeffner, K. N. Houk, S. M. Schulze and J. K. Lee, J. Org. Chem., 2003, 68, 2310-2316 describes recent treatments of anionic sigmatropic rearrangements using DFT methods in which biradical pathways appear significant. For an experimental observation of biradical character in the Cope rearrangement of a perhalogenated hexadiene, see: N. Y. Jing and D. M. Lemal, J. Am. Chem. Soc., 1993, 115, 8481-8482.
21. G. Dimartino, T. Gelbrich, M. B. Hursthouse, M. E. Light, J. M. Percy and N. S. Spencer, Chem. Commun., 1999, 2535-2536 describes the preliminary publication of these results.
22. L. R. Cox, G. A. DeBoos, J. J. Fullbrook, J. M. Percy, N. S. Spencer and M. Tolley, Org. Lett., 2003, 5, 337-339.
23. G. A. DeBoos, J. J. Fullbrook and J. M. Percy, Org. Lett., 2001, 3, 2859-2861.
24. G. A. DeBoos, J. J. Fullbrook, W. M. Owton, J. M. Percy and A. C. Thomas, Synlett, 2000, 963-966.
25. S. T. Patel, J. M. Percy and R. D. Wilkes, Tetrahedron, 1995, 51, 11327-11336.
26. S. T. Patel, J. M. Percy and R. D. Wilkes, J. Org. Chem., 1996, 61, 166-173.
27. M. J. Broadhurst, S. J. Brown, J. M. Percy and M. E. Prime, J. Chem. Soc., Perkin Trans. 1, 2000, 3217-3226.
28. G. Dimartino and J. M. Percy, Chem. Commun., 2000, 2339-2340.
29. W. Yuan, R. J. Berman and M. H. Gelb, J. Am. Chem. Soc., 1987, 109, 8071-8081.
30. F. Tellier, M. Audouin, M. Baudry and R. Sauvêtre, Tetrahedron Lett., 1998, 39, 5041-5044.
31. J. M. Bainbridge, S. J. Brown, P. N. Ewing, R. R. Gibson and J. M. Percy, J. Chem. Soc., Perkin Trans. 1, 1998, 2541-2545.
32. J. Burdon, P. L. Coe, I. B. Haslock and R. L. Powell, Chem. Commun., 1996, 49-50.
33. J. M. Bainbridge, S. Corr, M. Kanai and J. M. Percy, Tetrahedron Lett., 2000, 41, 971-974.
34. T. Dubuffet, R. Sauvêtre and J. F. Normant, J. Organomet. Chem., 1988, 341, 11-18.
35. J. A. Howarth, W M. Owton, J. M. Percy and M. H. Rock, Tetrahedron, 1995, 51, 10289-10302.
36. P. L. Coe, J. Burdon and I. B. Haslock, J. Fluorine Chem., 2000, 102, 43-50.
37. A. J. Mancuso, S.-L. Huang and D. Swern, J. Org. Chem., 1978, 43, 2480-2482.
38. R. C. Gadwood and R. M. Lett. J. Org. Chem., 1982, 47, 2268-2275.
39. E. C. Ashby and J. T. Laemmle, Chem. Rev., 1975, 75, 521-546.
40. M. Shimano and A. I. Meyers, Tetrahedron Lett., 1994, 35, 7727-7730.
41. J. Stonehouse, P. Adell, J. Keeler and A. J. Shaka, J. Am. Chem. Soc., 1994, 116, 6037-6038.
42. J. M. Warrington, G. P. A. Yap and L. Barriault, Org. Lett., 2000, 2, 663-665.
43. E. A. Basso, C. Kaiser, R. Rittner and J. B. Lambert, J. Org. Chem., 1993, 58, 7865-7869.
44. E. L. Eliel, S. H. Wilen and L. N. Mander, Stereochemistry of Organic Compounds, Wiley-Interscience, Chichester, 1994, 732-734.
45. J. W. Banks, A. S. Batsanov, J. A. K. Howard, D. O'Hagan, H. S. Rzepa and S. Martin-Santamaria, J. Chem. Soc., Perkin Trans. 2, 1999, 2409-2411.
46. D. A. Holt, Tetrahedron Lett., 1981, 22, 2243-2246.
47. E. N. Marvell and W. Whalley, Tetrahedron Lett., 1970, 509-512.
48. M. F. Lipton, C. M. Sorensen, A. C. Sadler and R. H. Shapiro, J. Organomet. Chem., 1980, 186, 155-158.