Thermal addition reaction of aroylketene with 1-aryl-1-trimethylsilyloxyethylenes: Aromatic substituent effects of aroylketene and aryltrimethylsilyloxyethylene on their reactivity

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 5, 1996, Pages 956-966

  Saitoh, Toshiaki ^a   Oyama, Taichi ^a   Sakurai, Kiyomi ^a   Niimura, Yosihiro ^a   Hinata, Mitsuru ^a   Horiguchi, Yoshie ^a   Toda, Jun ^a   Sano, Takehiro ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

4 pyrone; Aroylketene; Aryltrimethylsilyloxyethylene; Molecular orbital; Thermal addition reaction

Indexed keywords

4 PYRONE DERIVATIVE; KETENE DERIVATIVE; PENTANE 1,3,5 TRIONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; MOLECULAR DYNAMICS; TEMPERATURE DEPENDENCE;

EID: 0029956278     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.956     Document Type: Article

References (22)

1. For a review, see: Sato M., Yuki Gosei Kugaku Kyokai Shi, 46, 596-609 (1988); Wentrup C., Heilmayer W., Kollenz G., Synthesis, 1994, 1219-1248.
2. For a review, see: Sato M., Yuki Gosei Kugaku Kyokai Shi, 46, 596-609 (1988); Wentrup C., Heilmayer W., Kollenz G., Synthesis, 1994, 1219-1248.
3. Ziegler E., Eder M., Belegratis C., Prewedourakis E., Monatsh. Chem., 98, 2249-2251 (1967).
4. Capuano L., Kirn H. R., Zander R., Chem. Ber., 109, 2456-2461 (1976).
5. Andreichikov Y. S., Nekrasov D. D., Zh. Org. Khim., 20, 1775-1779 (1984); Andreichikov Y. S., Nekrasov D. D., Rudenko M. A., Vinokurova O. V., Khim. Geterotsikl Soedin SSR, 1989, 1265-1268.
6. Andreichikov Y. S., Nekrasov D. D., Zh. Org. Khim., 20, 1775-1779 (1984); Andreichikov Y. S., Nekrasov D. D., Rudenko M. A., Vinokurova O. V., Khim. Geterotsikl Soedin SSR, 1989, 1265-1268.
7. Hyatt J. A., Feldman P. L., Clemens R. J., J. Org. Chem., 49, 5105-5108 (1984).
8. Andreichikov Y. S., Gein V. L., Kozlov A. P., Vinokurova O. V., Zh. Org. Khim., 24, 210-217 (1988).
9. Capuano L., Bolz G., Burger R., Burkhardt V., Huch V., Justus Liebigs Ann. Chem., 1990, 239-243.
10. Sato M., Katagiri N., Takayama K., Hirose M., Kaneko C., Chem. Pharm. Bull., 37, 665-669 (1989).
11. Sato M., Ogasawara H., Kato K., Sakai M., Kato T., Chem. Pharm. Bull., 31, 4300-4305 (1983).
12. Wenkert E., Anantharayan T. P., Ferreira V. F., Hoffmann M. G., Kim H. S., J. Org. Chem., 55, 4975-4976 (1990).
13. Coleman R. S., Grant E. B., Tetrahedron Lett., 31, 3677-3680 (1990).
14. Sano T., Saitoh T., Toda J., Heterocycles, 36, 2139-2145 (1993).
15. Murai S., Hasegawa K., Sonoda N., Angew. Chem., Int. Ed. Engl., 14, 636-637 (1975).
16. Carrol M. F., Bader A. R., J. Am. Chem. Soc., 74, 6305 (1952); idem, ibid., 75, 5400-5402 (1953); Jäger G., Wenzelburger J., Justus Liebigs Ann. Chem., 1976, 1689-1712.
17. Carrol M. F., Bader A. R., J. Am. Chem. Soc., 74, 6305 (1952); idem, ibid., 75, 5400-5402 (1953); Jäger G., Wenzelburger J., Justus Liebigs Ann. Chem., 1976, 1689-1712.
18. Carrol M. F., Bader A. R., J. Am. Chem. Soc., 74, 6305 (1952); idem, ibid., 75, 5400-5402 (1953); Jäger G., Wenzelburger J., Justus Liebigs Ann. Chem., 1976, 1689-1712.
19. Zeller K. P., Meier H., Müller E., Tetrahedron, 28, 5831-5838 (1972).
20. Sauer J., Sustmann R., Angew. Chem. Int. Ed. Engl., 19, 779-807 (1980).
21. Semiempirical molecular orbital calculations were performed with PM3 Hamiltonian implemented in a MOPAC program (Cache Ver. 3.6). All geometries were fully optimized by an eigenvector-following routine (PRECISE option).
22. Light R. J., Hauser C. R., J. Org. Chem., 25, 538-546 (1960).