One-pot assembly of 7-methylene-6,8-dioxabicyclo[3.2.1]octanes, congeners of frontalin, from ketones and acetylene

European Journal of Organic Chemistry

Volumn , Issue 30, 2009, Pages 5142-5145

  Trofimov, Boris A ^a   Schmidt, Elena Yu ^a   Ushakov, Igor A ^a   Mikhaleva, Albina I ^a   Zorina, Nadezhda V ^a   Protsuk, Nadezhda I ^a   Senotrusova, Elena Yu ^a   Skital'Tseva, Elena V ^a   Kazheva, Olga N ^b   Alexandrov, Grigorii G ^c   Dyachenko, Oleg A ^b  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

^b INSTITUTE OF PROBLEMS OF CHEMICAL PHYSICS   (Russian Federation)

^c KURNAKOV INSTITUTE OF GENERAL AND INORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Alkynes; Ketones; Oxygen heterocycles; Pheromones; Superbasic systems

Indexed keywords

EID: 70350162339     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900853     Document Type: Article

References (23)

1. a) A E. Favorsky, Zh. Ross. Khun. Obshch. 1906, 37, 643;
2. b) B. A. Trofimov, Curr. Org. Chem. 2002, 5, 1121-1162;
3. c) M. Smith, I March, March's Advanced Organic Chemistry, 6th ed., Wiley, New York, 2007, p. 1360.
4. a) G. W Kinzer, A. F. Fentiman, T. F. Page, R. L. FoIz, J. P.Vite, G. B. Pitman, Nature 1969, 221, 447-478;
5. b) J. A. A. Renwick, I P. Vite, Nature 1969, 224, 1222-1223;
6. c) E. M. Suh, Y. Kishi, J. Am. Chem. Soc, 1994, 116, 11205-11206.
7. D. Basavaiah, J. S. Rao, R. J. Reddy, A. J. Rao, Chem. Commun. 2005, 2621-2623.
8. M. Yus, D. J Ramon, O. Prieto, Eur. J. Org. Chem. 2003, 2745-2748.
9. a) T. E. Perrin, L. E. L. Rasmussen, R. Gunawardena, R. A. Rasmussen, J. Chem. Ecol. 1996, 22, 207-221;
10. b) L. E. L. Rasmussen, H. S. Riddle, V. Krishnamurthy, Nature 2002, 415, 975-976.
11. D. P. W Huber, R. Cries, J. H. Borden, H. D. Pierce, J. Chem. Ecol. 1999, 25, 805-816.
12. S.C. Sinha, E. Reinan, J. Am. Chem. Soc. 1995, 117, 3653-3654.
13. K. Mori in Topics in Current Chemistry Vol. 239: Pheromone and Other Semiochemicals I (Ed.: S. Schulz), Springer, Heidelberg, 2004, pp. 1-50.
14. A. L. Sousa, I. S. Resck, J. Braz. Chem. Soc. 2002, 13, 233-237.
15. N. Ibrahim, T. Eggimann, E. A. Dixon, H. Wieser, Tetrahedron 1990, 46, 1503-1514.
16. B. A. Trofimov, Heteroatomic Derivatives of Acetylene: New Polyfunctional Monomers, Reagents, and Intermediates, Nauka, Moscow, 1981, p. 320 (in Russian).
17. J.I. Dickstein, S. I. Miller in The Chemistry of the Carbon-Carbon Triple Bond, Part 2 (Ed.: S. Patai), Wiley, New York, 1978, p. 814.
18. a) R.J. Tedeschi, Acetylene-Based Chemicals from Coal and Other Natural Resources, Marcel Dekher, New York, 1982;
19. b) W Reppe, Neue Entwicklungen auf dem Gebiete der Chemie des Acetylens und Kohlenoxyds, Springer, Berlin, 1949, p. 164;
20. c) J. W. Copenhaver, M. H. Bigelow, Acetylene and Carbon Monoxide Chemistry, Reinhold Publishing Corp., New York, 1949, p. 223.
21. B. A. Trofimov in Modern Problems of Organic Chemistry, St.Petersburg University Press, St.-Petersburg, 2004, issue 14, pp. 121-163.
22. F. G. Bordwell, G. E. Drucker, N. H. Andersen, A.D. Denniston, J. Am. Chem. Soc. 1986, 108, 7310-7313.
23. B. A. Trofimov, A.M. Vasil'tsov, S.V. Amosova, Izv. Akad. Nauk SSSR Ser. Khim. 1986, 4, 751-756.