Development in ketene chemistry: Generation and reaction of α-oxoketenes

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 57, Issue 2, 1999, Pages 76-83

  Sato, Masayuki ^a   Iwamoto, Ken Ichi ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

1,3 Dioxin 4 one; Cycloaddition; Cycloreversion; Thermal fragmentation; oxoketene

Indexed keywords

EID: 0002835235     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.57.76     Document Type: Article

References (92)

1. H. Staudinger, "Die Ketene", Enke, Stuttgart, 1912
2. (a) "The Chemistry of Ketenes, Allenes and Related Compounds", Part 1 and 2, S. Patai, Ed., John Wiley & Sons, New York, 1980;
3. (b) H. R. Seikaly, T.T. Tidwell, Tetrahedron, 42, 2587 (1986);
4. (c) T.T. Tidwell, "Ketenes", John Wiley & Sons, New York, 1995
5. T.T. Tidwell, Acc. Chem. Res., 23, 273 (1990);
6. A.D. Allen, J. Ma, M.A. McAllister, T.T. Tidwell, Q.-C. Zhao, Acc. Chem. Res., ibid., 28, 265 (1995)
7. (c) C. Kaneko, M. Sato, J. Sakaki, Y. Abe, J. Heterocycl. Chem., 27, 25 (1990);
8. (d) C. Wentrup, W. Heilmayer, G. Kollenz, Synthesis, 1994, 1219;
9. (e) C. Wentrup, B.E. Fulloon, D.W.J. Moloney, H. Bibas, M.W. Wong, Pure Appl. Chem., 68, 891 (1996)
10. H.W. Moore, O.H.W. Decker, Chem. Rev., 86, 821 (1986)
11. S. Ham, D.M. Birney, Tetrahedron Lett., 38, 5925 (1977)
12. K.K. Wang, Chem. Rev., 96, 207 (1996)
13. G. Jager, Wenzelburger, Liebigs Ann. Chem., 1982, 1753
14. M. Sato, N. Kanuma, T. Kato, Chem. Pharm. Bull., 30, 1315 (1982);
15. M. Sato, H. Ogasawara, E. Yoshizumi, T. Kato, Heterocycles, 17, 297 (1982)
16. (a) S. Murai, K. Hasegawa, N. Sonoda, Angew. Chem., Int. Ed.. Engl., 14, 636 (1975);
17. (b) G. Kollenz, E. Ziegler, W. Ott, G. Kriwetz, Z. Naturforsch., B: Anorg. Chem., Org. Chem., 32, 701 (1977)
18. [Chem. Abstr., 87, 201432 (1977)];
19. Y.S. Andreichikov, L.F. Gein, G. D. Plakhina, Zh. Org. Khim., 16, 2336 (1980)
20. [Chem. Abstr., 94, 156840 (1981)]
21. R. Leung-Toung, C. Wentrup, Tetrahedron, 48, 7641 (1992).
22. R.J. Clemens, J.S. Witzeman, J. Am. Chem. Soc., 111, 2186 (1989)
23. G. A. Cartwright, R.O. Gould, H. McNab, Chem. Commun., 1977, 1293
24. (a) M. Sato, H. Ogasawara, K. Takayama, C. Kaneko, Heterocycles, 26, 2611 (1987);
25. (b) M. Sato, J. Sakaki, K. Takayama, S. Kobayashi, M. Suzuki, C. Kaneko, Chem. Pharm. Bull., 38, 94 (1990)
26. (a) R.K. Boeckman, Jr., J.R. Pruitt, J. Am. Chem. Soc., 111, 8286 (1989);
27. (b) R.K. Boeckman, Jr., C.H. Weidner, R.B. Perni, J. J. Napier, J. Am. Chem. Soc., ibid., 111, 8036 (1989);
28. (c) N.A. Petasis, M.A. Patane, J. Chem. Soc., Chem. Commun., 1990, 836;
29. (d) C.C. Chen, E.K. Quinn, M.M. Olmstead, M.J. Kurth, J. Org. Chem., 58, 5011 (1993)
30. Y. Chiang, H.-X. Guo, A. J. Kresge, O. S. Tee, J. Am. Chem. Soc., 118, 3386 (1996)
31. H. McNab, Chem. Soc. Rev., 7, 345 (1978);
32. B. -C. Chen, Heterocycles, 32, 529 (1991)
33. Y. Oikawa, K. Sugano, O. Yonemitsu, J. Org. Chem., 43, 2087 (1978)
34. Y. Hamada, Y. Kondo, M. Shibata, T. Shioiri, J. Am. Chem. Soc., 111, 669 (1989);
35. J. Maibaun, D.H. Rich, J. Med. Chem., 32, 1571 (1989);
36. S. Hamilakis, D. Kontonassios, C. Sandris, J. Heterocycl. Chem., 33, 825 (1996)
37. (a) M. Sato, H. Ogasawara, K. Oi, T. Kato, Chem. Pharm. Bull., 31, 1896 (1983);
38. (b) M. Sato, K. Sekiguchi, H. Ogasawara, C. Kaneko, Synthesis, 1985, 224;
39. (c) M. Sato, N. Yoneda, C. Kaneko, Chem. Pharm. Bull., 34, 4577 (1986)
40. M. Sato, M. Murakami, C. Kaneko, Tetrahedron, 49, 8529 (1993);
41. M. Sato, M. Murakami, S. Sunami, C. Kaneko, T. Furuya, H. Kurihara, J. Am. Chem. Soc., 117, 4279 (1995)
42. C. L. Perrin, T. Arrhenius, J. Am. Chem. Soc., 100, 5249 (1978)
43. M. Sato, H. Ban, C. Kaneko, Tetrahedron Lett., 38, 6689 (1997)
44. M. Sato, N. Yoneda, N. Katagiri, H. Watanabe, C. Kaneko, Synthesis, 1986, 672
45. K. Pihlaja, M. Seilo, Acta Chem. Scand., 23, 3003 (1969)
46. (a) G.A. Bihlmayer, P. Schuster, O.E. Polansky, Monatsh. Chem., 96, 145 (1966);
47. (b) K. Matoba, T. Yamazaki, Chem. Pharm. Bull., 31, 2955 (1983)
48. Y. Morita, R. Kamakura, M. Takeda, Y. Yamamoto, Chem. Commun., 1997, 359
49. J. Boivin, L.E. Kaim, S.Z. Zard, Tetrahedron, 51, 2585 (1995)
50. E. Schaumann, Tetrahedron, 44, 1827 (1988)
51. M. Sato, H. Ban, F. Uehara, C. Kaneko, J. Chem. Soc., Chem. Commun., 1996, 775
52. M. Ohno, M. Itoh, T. Eguchi, Synthesis, 1993, 793;
53. M. Pomerantz, M. Levanon, X. Gu, H. V. Dias, Tetrahedron, 53, 10019 (1997)
54. J. Toda, T. Saitoh, T. Oyama, Y. Horiguchi, T. Sano, Heterocycles, 43, 2457 (1996)
55. S.-G. Hong, X.-Y. Fu, THEOCHEM, 209, 241 (1990)
56. (a) D.M. Birney, P.E. Wagenseller, J. Am. Chem. Soc., 116, 6262 (1994);
57. (b) P.E. Wagenseller, D.M. Birney, D. Roy, J. Org. Chem., 60, 2853 (1995);
58. (c) S. Ham, D.M. Birney, J. Org. Chem., ibid., 61, 3962 (1996);
59. (d) D.M. Birney, X. Xu, S. Ham, X. Huang, J. Org. Chem., ibid., 62, 7114 (1997)
60. S.W.E. Eisenberg, M. J. Kurth, W.H. Fink, J. Org. Chem., 60, 3736 (1995)
61. D. Seebach, J. Zimmermann, U. Gysel, R. Ziegler, T.-K. Ha, J. Am. Chem. Soc., 119, 4763 (1988);
62. M.G. Organ, R.D.J. Froese, J.D. Goddard, N. J. Taylor, G.L. Lange, J. Am. Chem. Soc., ibid., 116, 3312 (1994);
63. M. Sato, S. Sunami, C. Kaneko, Heterocycles, 42, 861 (1996)
64. M. Sato, H. Ogasawara, E. Yoshizumi, T. Kato, Chem. Pharm.Bull., 31, 1902 (1983)
65. R. C.-Y. Liu, J. Lusztyk, M.A. MacAllister, T.T. Tidwell, B.D. Wagner, J. Am. Chem. Soc., 120, 6247 (1998)
66. C. Wentrup, K.-P. Netsch, Angew. Chem., Int. Ed. Engl., 23, 802 (1984)
67. (a) B. Fulloon, H.A.A. El-Nabi, G. Kollenz, C. Wentrup, Tetrahedron Lett., 36, 6547 (1995);
68. (b) D.W. Moloney, M.W. Wong, R. Flammang, C. Wentrup, J. Org. Chem., 62, 4240 (1997)
69. M.W. Wong, C. Wentrup, J. Org. Chem., 59, 5279 (1994);
70. R. Koch, M.W. Wong, C. Wentrup, J. Org. Chem., ibid., 61, 6809 (1996);
71. J. Finnerty, J. Andraos, Y. Yamamoto, M.W. Wong, C. Wentrup, J. Am. Chem. Soc., 120, 1701 (1998)
72. K. Nakatani, J. Shirai, S. Sando, I. Saito, J. Am. Chem. Soc., 119, 7626 (1997)
73. F.J. Zawacki, M.T. Crimmins, Tetrahedron Lett., 37, 6499 (1996);
74. M.A. D'Annibale, A. Pesce, S. Resta, C. Trogolo, Tetrahedron Lett., ibid., 37, 7429 (1996);
75. Y. Morita, M. Kaneko, S. Matsuzawa, Y. Yamamoto, J. Heterocycl. Chem., 34, 515 (1997);
76. J. Quiroga, A. Hormaza, B. Insuasty, M. Nogueras, A. Sanchez, N. Hanold, H. Meier, J. Heterocycl. Chem., ibid., 34, 521 (1997);
77. I. Yildirim, I.O. Ilhan, , J. Heterocycl. Chem., ibid. 34, 1047 (1997);
78. F.T. Coppo, M. Fawzi, J. Heterocycl. Chem., ibid., 34, 729 (1997);
79. J. Toda, T. Saitoh, T. Sano, Heterocycles, 45, 1937 (1997)
80. J.E. Baldwin, J. Org. Chem., 28, 3112 (1963);
81. J.A. Hyatt, P.L. Feldman, R.J. Clemens, J. Org. Chem., 49, 5105 (1984)
82. Vol.J. Org. Chem., 2, p.86, (1998), M. Sato, F. Uehara, K. Sato, M. Yamaguchi, C. Kabuto, in contribution
83. A.R. Katritzky, C.W. Rees, "Comprehensive Heterocyclic Chemistry", Vol.3, pp.573-884, Pergamon Press, 1984;
84. D. Barton, W.D. Ollis, "Comprehensive Organic Chemistry", Vol.4, pp. 629-691, Pergamon Press, 1979
85. R.M. Izatt., K. Pawlak, J.S. Bradshaw, Chem. Rev., 95, 2529 (1995);
86. X.X. Zhang, J.S. Bradshaw, R.M. Izatt, Chem. Rev., ibid., 97, 3313 (1997);
87. K.T. Toh, L. Delaude, R. Breslow, J. Am. Chem. Soc., 116, 11234 (1994);
88. N. Kanomata, T. Nakata, Angew. Chem., Int. Ed. Engl., 36, 1207 (1997)