Base catalysed rearrangements involving ylide intermediates. part 6. the rearrangements of diallyl- and allyipropynyl-ammonium cations in protic media

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue , 1980, Pages 1477-1486

  Laird, Trevor ^a   Ollis, W David ^a   Sutherland, Ian O ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049107029     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19800001477     Document Type: Article

References (53)

1. Part 5, T. Laird, W. D. Ollis, and I. O. Sutherland, preceding paper.
2. Preliminary communication, T. Laird and W. D. Ollis, J.C.S. Chem. Comm., 1972, 557.
3. Part 1, R. W. Jemison, T. Laird, W. D. Ollis, and I. O. Sutherland, J.C.S. Perkin I, 1980, 1436.
4. V. Rautenstrauch, Helv. Chim. Acta, 1972, 55, 2233.
5. T. L. Gilchrist and R. C. Storr, ‘Organic Reactions and Orbital Symmetry,’ Cambridge University Press, London, 1972, pp. 234-240;
6. Nguyen Tron Anh, ‘Die Woodward-Hoffmann, Regeln und ihre Anwendung,’ Verlag Chemie, Weinheim, 1972, pp. 96-98.
7. S. H. Pine, Org. Reactions, 1970, 18, 403;
8. A. R. Lepley and G. Giumanini, in ‘Mechanisms of Molecular Migration,’ ed.
9. S. Thyagarajan, Interscience, New York, 1971, vol. 3, p. 297;
10. T. S. Stevens and W. E. Watts, ‘Selected Molecular Rearrangements,’ van Nostrand-Reinliold, London, 1973, p. 81.
11. A. T. Babayan and M. H. lndjikyan, Tetrahedron, 1964, 20, 1371 and references cited therein.
12. T. S. Stevens, Progr. Org. Chem., 1968, 7, 48.
13. M. Riviere and A. Lattes, Bull. Soc. chim. France, 1972, 730;
14. J. Sauer and H. Prahl, Tetrahedron Letters, 1966, 2863 and references cited therein.
15. W. von E. Doering and W. R. Roth, Tetrahedron, 1962, 18, 67;
16. W. von E. Doering and W. R. Roth, Angew. Chem. Internat. Edn., 1963, 2, 115;
17. S. J. Rhoads, in ‘Molecular Rearrangements,’ ed. P. de Mayo, Interscience, New York, 1963, Part 1, p. 655;
18. E. Winterfeldt, Fortschr. Chem. Forsch., 1970, 16, 75;
19. H. J. Hansen and H. Schmid, Chem. In Britain, 1969, 5, 111.
20. E. Elkik, Bull. Soc. chim. France, 1960, 972; 1969, 903;
21. K. C. Brannock and R. D. Burpitt, J. Org. Chem., 1961, 26 3576;
22. G. Opitz, Annalen, 1961, 650, 122;
23. J. Corbier, Compt. rend., 1969, 268C, 1614; 1970, 270C, 2077;
24. R. K. Hill and H. N. Khatri, Tetrahedron Letters, 1978, 4337.
25. I. Iwai, in ‘of Molecular Migrations,’ ed. B. S. Thyagarajan, Interscience, New York, 1969, vol. 2, p. 73;
26. G. D. Appleyard and C. J. M. Stirling, J. Chem. Soc. (C), 1969, 1904;
27. R. J. Bushby, Quart. Rev., 1970, 24, 585.
28. H. Christol, R. Jacquier, and M. Mousseron, Bull. Soc. chim. France, 1958, 248.
29. W. R. Brasar and C. R. Hauser, Org. Synth., 1963, Coll. Vol. 4, p. 508.
30. I. O. Sutherland, Ann. Reports N.M.R. Spectroscopy, 1971, 4, 192;
31. H. Kessler, Angew. Chem. Internat. Edn., 1970, 9, 219.
32. G. Gamboni, V. Theus, and H. Schinz, Helv. Chim. Acta, 1955, 38, 255.
33. R. K. Bentley, U. Graf, E. R. H. Jones, R. A. M. Moss, V. Thailer, and R. A. Vere Hodge, Chem. Soc. (C), 1969, 683;
34. J. Elguero, R. Jacquier, and C. Marzin, Bull. Soc. chim. France, 1967, 3005;
35. J. M. F. Gagan, A. G. Lane, and D. Lloyd, J. Chem. Soc. (C), 1970, 2484;
36. R. C. Klinck and J. B. Stothers, Canad. J. Chem., 1966, 44, 45.
37. R. E. Rondeau and R. E. Sievers, J. Amer. Chem. Soc., 1971, 93, 1522.
38. J. W. de Haan and L. J. M. van de Ven, Tetrahedron Letters, 1971, 2703;
39. C. Beauté, Z. W. Wolkowski, J. P. Merda, and Ü. Lelandais, Tetrahedron Letters, 1971, p. 2473;
40. H. G. Richey and F. W. von Rein, Tetrahedron Letters, 1971., p. 3781.
41. R. B. Woodward and R. Hoffmann, Angew. Chem. Internat. Edn., 1969, 8, 781;
42. R. Hoffmann, C. C. Levin, and R. A. Moss, J. Amer. Chem. Soc., 1973, 95, 629.
43. L. H. Klemm, T. M. McGuire, and K. W. Gopinath, J. Org. Chem., 1976, 41, 2571.
44. M. T. Cox, J.C.S. Chem. Comm., 1975, 903.
45. W. Oppolzer, R. Achini, E. Pfenninger, and H. P. Weber, Helv. Chim. Acta, 1976, 59, 1186.
46. W. Oppolzer, Angew. Chem. Internat. Edn., 1977, 16, 10.
47. I. Iwai and J. Ide, Chem. and Pharm. Bull. (Japan), 1964, 12, 1094.
48. P. J. Garratt and S. B. Neoh, J. Amer. Chem. Soc., 1975, 97, 3255.
49. I. Iwai and J. Ide, Chem. and Pharm. Bull. (Japan), 1963, 11, 1556, 1564.
50. A. J. Bartlett, T. Laird, and W. D. Ollis, J.C.S. Chem. Comm., 1974, 496;
51. A. J. Bartlett, T. Laird, and W. D. Ollis, J.C.S. Perkin I, 1975, 1315.
52. C. H. Mannich and H. Davidsen, Ber., 1936, 69, 2106.
53. L. H. Klemm, Hsu Lee, K. W. Gopinath, and C. E. Klopfenstein, J. Org. Chem., 1966, 31. 2376.