Synthesis of Cyclic and Acyclic Enol Ethers (Vinyl Ethers)

Journal of Organic Chemistry

Volumn 58, Issue 6, 1993, Pages 1449-1457

  Gassman, Paul G ^a   Burns, Stephen J ^a   Pfister, Keith B ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751386385     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00058a027     Document Type: Article

References (60)

1. For leading references, see: (a) Wohl, R. A. Synthesi. 1974, 38.
2. Cookson, R. C.; Singh, P. J. Chem. Soc. 1971, 1477.
3. Schank, K.; Pack, W. Chem. Ber. 1969, 102, 1892.
4. Lindsay, D. G.; Reese, C. B. Tetrahedron. 1965, 21, 1673.
5. Meerwin, H. In Houben-Weyl, Methoden der Organische Chemie; Muller, E., Ed.; Georg Thieme Verlag: Stuttgart, 1965; Vol. 6/3, p 199ff.
6. Miller, R. D.; McKean, D. R. Tetrahedron Lett. 1982, 23, 323.
7. Marsi, M.; Gladysz, J. A. Organometallic. 1982, 1, 1467.
8. Marsi, M.; Gladysz, J. A. Tetrahedron Lett. 1982, 23, 631.
9. Gladysz, J. A.; Williams, C.; Tam, W.; Johnson, D.; Parker, D.; Selover, J. Inorg. Chem. 1979, 18, 553.
10. Naruse, Y.; Yamamoto, H. Tetrahedron Lett. 1986, 27, 1363.
11. Katritzky, A. R.; Bayyuk, S. I.; Rachwal, S. Synthesis. 1991, 279.
12. Mandai, T.; Hara, K.; Nakajima, T.; Kawada, M.; Otera, J. Tetrahedron Lett. 1983, 24, 4993.
13. Riediker, M.; Schwartz, J. J. Am. Chem. Soc. 1982, 104, 5842.
14. Mulzer, J.; Pointner, A.; Chuckolowski, A.; Bruntrup, G. J. Chem. Soc., Chem. Commun. 1979, 52.
15. Kluge, A. F. Tetrahedron Lett. 1978, 3629.
16. Julia, M.; Righini, A.; Uguen, D. J. Chem. Soc., Perkin Trans. 1. 1978, 1646.
17. Noyori, R.; Murata, S.; Suzuki, M. Tetrahedron Lett. 1981, 37, 3899.
18. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357.
19. See also: Hwu, J. R.; Wetzel, J. M. J. Org. Chem. 1985, 50, 3946.
20. Gassman, P. G.; Burns, S. J. J. Org. Chem. 1988, 53, 5576.
21. For a preliminary report of part of this investigation, see: Gassman, P. G.; Burns, S. J. J. Org. Chem. 1988, 53, 5574.
22. For subsequent applications and studies of our reaction, see: Sundberg, R. J.; Cherney, R. J. J. Org. Chem. 1990, 55, 6028.
23. Rychnovsky, S.; Kim, J. Tetrahedron Lett. 1991, 32, 7219, 7223.
24. Sundberg, R. J.; Gadamasetti, K. G. Tetrahedron, 1991, 47, 5673.
25. Fioravanti, S.; Loreto, M. A.; Pellacani, L.; Tardella, P. A. Tetrahedron. 1991, 47, 5877.
26. Emde, H.; Domsch, D.; Feger, H.; Frick, U.; Gotz, A.; Hergott, H.; Hofmann, K.; Kober, W.; Krageloh, K.; Oesterle, T.; Steppan, W.; West, W.; Simchen, G. Synthesis. 1982, 1.
27. Gorman, A. A.; Gould, I. R.; Hamblett, I. J. Am. Chem. Soc. 1982, 104, 7098.
28. Lorette, N. B.; Howard, W. L.; Brown, J. H., Jr. J. Org. Chem. 1959, 24, 1731.
29. Zajac, W. W., Jr.; Byrne, K. J. J. Org. Chem. 1970, 35, 3375.
30. Olah, G.; Narang, S. C.; Meidar, D.; Salem, G. F. Synthesis. 1981, 282.
31. McConaghy, J. S., Jr.; Bloomfield, J. J. J. Org. Chem. 1968, 33, 3425.
32. Traylor, T. G.; Perrin, C. L. J. Am. Chem. Soc. 1966, 88, 4934.
33. Taylor, R. J. Chem. Soc., Perkins Trans. 2. 1988, 737.
34. Huggins, M. J.; Kubier, D. G. J. Org. Chem. 1983, 48, 2813.
35. Kropp, P. J.; Pienta, N. J. J. Org. Chem. 1983, 48, 2084.
36. For example, see: Salmi, E. J. Chem. Ber. 1958, 71, 1805.
37. Micovic, V. M.; Stojiljkovic, A. Tetrahedron. 1958, 4, 186.
38. Sulzbacher, M.; Bergmann, E.; Pariser, E. R. J. Am. Chem. Soc. 1948, 70, 2827.
39. Treibs, W.; Grossman, P. Chem. Ber. 1959, 92, 267.
40. Allenger, N. L.; Juidal, S. P.; DaRooge, M. A. J. Org. Chem. 1962, 27 4290.
41. Zajac, W. W., Jr.; Rhu, B.; Brown, R. K. Can. J. Chem. 1966, 44, 1547.
42. Baudin, G.; Bowdon, D.; Pietrasanta, Y.; Pucci, B. Tetrahedron. 1978, 34, 3269.
43. Thuy, V. M.; Maitte, P. Bull. Chim. Soc. Fr. 1975 11–12, 2558.
44. Marton, D.; Slaviero, P.; Taglianini, G. Gazz. Chim. Ital. 1989 119 (6), 359.
45. Chien, J.-C.; Lillya, C.P.; Xu, B.B. J. Polymer Sci. Part A: Polym. Chem. 1986, 24, 2903.
46. Burford, C.; Cooke, F.; Roy, G.; Magnus, P. Tetrahedron. 1983, 39, 867.
47. Hahn, E. F. J. Org. Chem. 1973, 38, 2092.
48. Harper, R. J.; Newman, M. S. J. Am. Chem. Soc. 1958, 80, 6350.
49. Pallos, V. L.; Budai, Z.; Zolyami, G. Arzeim. Forsch. 1972, 22, 1505.
50. Conan, J.-Y.; Natat, A.; Priolet, D. Bull. Soc. Chim. Fr. 1976, 11–12, 1935.
51. Coene, E.; Anteunis, M. Bull. Soc. Chim. Belg. 1970, 8, 37.
52. Verzele, M.; Acki, M.; Anteunis, M. J. Chem. Soc. 1963, 5598.
53. Murai, S.; Aya, T.; Reuge, T.; Ryu, I.; Sonoda, N. J. Org. Chem. 1974 3. 85.
54. Rogic, M. M.; Swordloff, M. D.; Demmin, T. R. U.S. Patent 4,-045,422, 1977.
55. Barluenga, J.; Aznar, F.; Bayod, M. Synthesis. 1988, 2144.
56. Rhoads, S. J.; Chattopadhyay, K.; Waali, E. J. Org. Chem. 1970, 35, 3352.
57. Greenwald, R.; Chaykovsky, M.; Corey, E. J. J. Org. Chem. 1963, 28, 1128.
58. Rosseau, G.; LePerchec, P.; Conia, J. M. Synthesis. 1978, 67.
59. Akelah, A. Eur. Polym. J. 1982, 18, 559.
60. Reich, H. J.; Chow, F.; Shale, S. K. J. Am. Chem. Soc. 1979, 101, 6638.