The synthesis of alkenes via epi-phosphonium species: 2. A phosphorus Ramberg-Backlund reaction

Tetrahedron

Volumn 54, Issue 50, 1998, Pages 15361-15370

  Lawrence, Nicholas J ^a   Muhammad, Faiz ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Alkenes; Phosphonium salts; Polymethylhydrosiloxane; Ramberg Backlund reaction

Indexed keywords

ALKENE; N BROMOSUCCINIMIDE; PHOSPHONIUM DERIVATIVE; PHOSPHORUS; PIPERIDINE DERIVATIVE; SILOXANE; STILBENE; TITANIUM;

ARTICLE; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032506597     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00960-0     Document Type: Article

References (54)

1. 1 Lawrence, N. J.; Muhammad, F. Tetrahedron, 1998, 54, 15345.
2. 2 Dilworth, B. M.; McKervey, M. A. Tetrahedron, 1986, 42, 3731; Schank, K. in "The Chemistry of Sulfones and Sulfoxides," ed. Patai, S.; Rappoport, Z.; Stirling, C. J. M.; John Wiley, New York, 1988, Chap. 7, p. 165; Paquette, L. A. Org. React. (N.Y.), 1977, 25, 73; Ramberg, L.; Bäcklund, B. Ark. Kemi Mineral Geol., 1940, 13A, 27; Chem. Abs., 1940, 34, 4725; Clough, J. M., The Ramberg-Bäcklund Rearrangement' in Comprehensive Organic Synthesis; ed. Heathcock, C. H., Pergamon, 1991; vol. 3, pp. 861-886.
3. 2 Dilworth, B. M.; McKervey, M. A. Tetrahedron, 1986, 42, 3731; Schank, K. in "The Chemistry of Sulfones and Sulfoxides," ed. Patai, S.; Rappoport, Z.; Stirling, C. J. M.; John Wiley, New York, 1988, Chap. 7, p. 165; Paquette, L. A. Org. React. (N.Y.), 1977, 25, 73; Ramberg, L.; Bäcklund, B. Ark. Kemi Mineral Geol., 1940, 13A, 27; Chem. Abs., 1940, 34, 4725; Clough, J. M., The Ramberg-Bäcklund Rearrangement' in Comprehensive Organic Synthesis; ed. Heathcock, C. H., Pergamon, 1991; vol. 3, pp. 861-886.
4. 2 Dilworth, B. M.; McKervey, M. A. Tetrahedron, 1986, 42, 3731; Schank, K. in "The Chemistry of Sulfones and Sulfoxides," ed. Patai, S.; Rappoport, Z.; Stirling, C. J. M.; John Wiley, New York, 1988, Chap. 7, p. 165; Paquette, L. A. Org. React. (N.Y.), 1977, 25, 73; Ramberg, L.; Bäcklund, B. Ark. Kemi Mineral Geol., 1940, 13A, 27; Chem. Abs., 1940, 34, 4725; Clough, J. M., The Ramberg-Bäcklund Rearrangement' in Comprehensive Organic Synthesis; ed. Heathcock, C. H., Pergamon, 1991; vol. 3, pp. 861-886.
5. 2 Dilworth, B. M.; McKervey, M. A. Tetrahedron, 1986, 42, 3731; Schank, K. in "The Chemistry of Sulfones and Sulfoxides," ed. Patai, S.; Rappoport, Z.; Stirling, C. J. M.; John Wiley, New York, 1988, Chap. 7, p. 165; Paquette, L. A. Org. React. (N.Y.), 1977, 25, 73; Ramberg, L.; Bäcklund, B. Ark. Kemi Mineral Geol., 1940, 13A, 27; Chem. Abs., 1940, 34, 4725; Clough, J. M., The Ramberg-Bäcklund Rearrangement' in Comprehensive Organic Synthesis; ed. Heathcock, C. H., Pergamon, 1991; vol. 3, pp. 861-886.
6. 2 Dilworth, B. M.; McKervey, M. A. Tetrahedron, 1986, 42, 3731; Schank, K. in "The Chemistry of Sulfones and Sulfoxides," ed. Patai, S.; Rappoport, Z.; Stirling, C. J. M.; John Wiley, New York, 1988, Chap. 7, p. 165; Paquette, L. A. Org. React. (N.Y.), 1977, 25, 73; Ramberg, L.; Bäcklund, B. Ark. Kemi Mineral Geol., 1940, 13A, 27; Chem. Abs., 1940, 34, 4725; Clough, J. M., The Ramberg-Bäcklund Rearrangement' in Comprehensive Organic Synthesis; ed. Heathcock, C. H., Pergamon, 1991; vol. 3, pp. 861-886.
7. 2 Dilworth, B. M.; McKervey, M. A. Tetrahedron, 1986, 42, 3731; Schank, K. in "The Chemistry of Sulfones and Sulfoxides," ed. Patai, S.; Rappoport, Z.; Stirling, C. J. M.; John Wiley, New York, 1988, Chap. 7, p. 165; Paquette, L. A. Org. React. (N.Y.), 1977, 25, 73; Ramberg, L.; Bäcklund, B. Ark. Kemi Mineral Geol., 1940, 13A, 27; Chem. Abs., 1940, 34, 4725; Clough, J. M., The Ramberg-Bäcklund Rearrangement' in Comprehensive Organic Synthesis; ed. Heathcock, C. H., Pergamon, 1991; vol. 3, pp. 861-886.
8. 3 Lawrence, N. J.; Muhammad, F. Tetrahedron Lett., 1994, 35, 5903.
9. 4 Kosolapoff, G. M. "Organophosphorus compounds," Wiley, New York, 1950, p. 104.
10. 5 Fenton, G. W.; Ingold, C. K. J. Chem. Soc., 1929, 2342.
11. 6 Brophy, J. J.; Freeman, K. L.; Gallagher, M. J. J. Chem. Soc. (C), 1968, 2760.
12. 7 Horner, L.; Balzer, W. D. Tetrahedron Lett., 1965, 1157.
13. 8 Berk, S. C.; Buchwald, S. L. J. Org. Chem., 1992, 57, 3751;
14. Reding, M. T.; Buchwald, S. L. J. Org. Chem., 1995, 60, 7884.
15. 9 "Sigma-Aldrich Library of Chemical Safety Data," Ed. R. E. Longa, 2nd. ed, 1988, vol. 2, Sigma-Aldrich.
16. 10 Berk, S. C.; Buchwald, S. L. J. Org. Chem., 1993, 58, 3221.
17. 11 Coumbe, T.; Lawrence, N. J.; Muhammad, F. Tetrahedron Lett., 1994, 35, 625.
18. 12 Breeden, S. W.; Lawrence, N. J. Synlett., 1994, 833.
19. 13 Cristau, H.-J.; Ribeill, Y. Synthesis, 1988, 911.
20. 14 Breslow, R.; Deuring, L. A. Tetrahedron Lett., 1984, 25, 1345.
21. 15 Chan, T. L., Fong, S.; Li, Y.; Man, T. O.; Poon, C. D. J. Chem. Soc., Chem. Commun., 1994, 1771.
22. 16 Meyers, C. Y.; Malte, A. M.; Matthews, W. S. J. Am. Chem. Soc., 1969, 97, 7510.
23. 17 McKenna, E. G.; Walker, B. J. Tetrahedron Lett., 1988, 29, 485; McKenna, E. G.; Walker, B. J. J. Chem. Soc., Chem. Commun., 1989, 568.
24. 17 McKenna, E. G.; Walker, B. J. Tetrahedron Lett., 1988, 29, 485; McKenna, E. G.; Walker, B. J. J. Chem. Soc., Chem. Commun., 1989, 568.
25. 18 Hartley, F. R. The Chemistry of Organophosphorus Compounds, 1994, 3, 109.
26. 19 Johnson, A. W.; Kyllingstad, V. L. J. Org. Chem., 1966, 31, 334; Bergelson, L. D.; Barsukov, L. I.; Shemyakin, M. M. Tetrahedron, 1967, 23, 2709; Allen, D. W.; Ward, H. Tetrahedron Lett., 1979, 2707; McEwen, W. E.; Cooney, J. V. J. Org. Chem., 1983, 48, 983.
27. 19 Johnson, A. W.; Kyllingstad, V. L. J. Org. Chem., 1966, 31, 334; Bergelson, L. D.; Barsukov, L. I.; Shemyakin, M. M. Tetrahedron, 1967, 23, 2709; Allen, D. W.; Ward, H. Tetrahedron Lett., 1979, 2707; McEwen, W. E.; Cooney, J. V. J. Org. Chem., 1983, 48, 983.
28. 19 Johnson, A. W.; Kyllingstad, V. L. J. Org. Chem., 1966, 31, 334; Bergelson, L. D.; Barsukov, L. I.; Shemyakin, M. M. Tetrahedron, 1967, 23, 2709; Allen, D. W.; Ward, H. Tetrahedron Lett., 1979, 2707; McEwen, W. E.; Cooney, J. V. J. Org. Chem., 1983, 48, 983.
29. 19 Johnson, A. W.; Kyllingstad, V. L. J. Org. Chem., 1966, 31, 334; Bergelson, L. D.; Barsukov, L. I.; Shemyakin, M. M. Tetrahedron, 1967, 23, 2709; Allen, D. W.; Ward, H. Tetrahedron Lett., 1979, 2707; McEwen, W. E.; Cooney, J. V. J. Org. Chem., 1983, 48, 983.
30. 20 Yamataka, H.; Nagareda, K.; Ando, K.; Hanafusa, T. J. Org. Chem., 1992, 57, 2865.
31. 21 Ward, Jr., W. J.; McEwen, W. E. J. Org. Chem., 1990, 55, 493.
32. 22 Wadsworth Jr., W. S.; Emmons, W. D. J. Am. Chem. Soc., 1961, 83, 1733.
33. 23 Hockless, D. C. R.; Kang, Y. B.; McDonald, M. A.; Pabel, M.; Willis, A. C.; Wild, S. B. Organometallics, 1996, 15, 1301; Li, X.; Robinson, K. D.; Gaspar, P. P. J. Org. Chem., 1996, 61, 7702; Huy, N. H. T.; Mathey, F. Synlett, 1995, 353 and references therein.
34. 23 Hockless, D. C. R.; Kang, Y. B.; McDonald, M. A.; Pabel, M.; Willis, A. C.; Wild, S. B. Organometallics, 1996, 15, 1301; Li, X.; Robinson, K. D.; Gaspar, P. P. J. Org. Chem., 1996, 61, 7702; Huy, N. H. T.; Mathey, F. Synlett, 1995, 353 and references therein.
35. 23 Hockless, D. C. R.; Kang, Y. B.; McDonald, M. A.; Pabel, M.; Willis, A. C.; Wild, S. B. Organometallics, 1996, 15, 1301; Li, X.; Robinson, K. D.; Gaspar, P. P. J. Org. Chem., 1996, 61, 7702; Huy, N. H. T.; Mathey, F. Synlett, 1995, 353 and references therein.
36. 24 Hockless, D. C. R.; McDonald, M. A.; Pabel, M.; Wild, S. B. J. Chem. Soc., Chem. Commun., 1995, 257.
37. 25 Denney, D. B.; Shih, L. S. J. Am. Chem. Soc., 1974, 96, 317.
38. 26 Heuschmann, M.; Quast., H. Chem. Ber., 1982, 115, 3384.; Quast, H. Heuschmann, M. Angew. Chem. Int. Ed. Engl., 1978, 17, 867.
39. 26 Heuschmann, M.; Quast., H. Chem. Ber., 1982, 115, 3384.; Quast, H. Heuschmann, M. Angew. Chem. Int. Ed. Engl., 1978, 17, 867.
40. 27 Fry, A. J.; Chung, L.-L. Tetrahedron Lett., 1976, 645.
41. 28 Mitchell, R. H. Tetrahedron Lett., 1973, 4395.
42. 29 Weinges, K.; Klein, J.; Sipos, W.; Günther, P.; Huber-Patz, U.; Rodewald, H.; Deuter, J.; Irngartinger, H. Chem. Ber., 1986, 119, 1540.
43. 30 Johnson, C. R.; Corkins, H. G. J. Org. Chem., 1978, 43, 4140.
44. 31 Ramirez, F.; Desai, N. B.; Hansen, B.; McKelvie, N. J. Am. Chem. Soc., 1961, 83, 3539.
45. 32 Savage, M. P.; Trippelt, S. J. Chem. Soc. (C), 1968, 591.
46. 33 Griffin, C. E.; Gordon, M. J. Organomet. Chem., 1965, 3, 414.
47. 34 Burkow, I. C.; Sydnes, L. K.; Ubeda, D. C. N. Acta. Chem. Scand., 1987, B41, 235.
48. 35 Bachelor, F. W.; Loman, A. A.; Snowdon, L. R. Can. J. Chem., 1970, 48, 1554.
49. 36 Tokura, N.; Nagai, T.; Matsumura, S. J. Org. Chem., 1966, 31, 349.
50. 37 Binkley, R. W. J. Org. Chem., 1969, 34, 931.
51. 38 James, B. G.; Pattenden, G.; J. Chem. Soc., Perkin Trans. 1, 1974, 1195.
52. 39 Bergmann, F.; Schapiro, D. J. Org. Chem., 1947, 12, 57.
53. 40 Zechmeister, L.; McNeely, W. H. J. Am. Chem. Soc., 1942, 64, 1919.
54. 41 Hoeg, D. F.; Lusk, D. I. J. Organomet. Chem., 1966, 5, 1.