Unexpected formation of 2,3,7-triphenylcyclopenta[c]pyran from the reaction of 1,2-diphenylethanedione (benzil) with cyclopentadiene

Revue Roumaine de Chimie

Volumn 47, Issue 8-9, 2002, Pages 705-713

  Banciu, Mircea D ^a   Balaban, Alexandra T ^a,e   Drǎghici, Constantin ^b   Haiduc, Ionel ^c   Ivanciuc, Ovidiu ^d  

^a UNIVERSITY POLITEHNICA OF BUCHAREST   (Romania)

^b ACADEMY OF ROMANIAN SCIENTISTS   (Romania)

^c BABE BOLYAI UNIVERSITY   (Romania)

^d UNIVERSITY OF TEXAS MEDICAL BRANCH   (United States)

^e TEXAS A AND M UNIVERSITY AT GALVESTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; DATA REDUCTION; DEHYDROGENATION; NUCLEAR MAGNETIC RESONANCE; SODIUM COMPOUNDS; SUBSTITUTION REACTIONS; X RAY CRYSTALLOGRAPHY;

BOND LENGTH; CYCLOPENTADIENE; IRIDOIDS; PROTONATION;

ORGANIC ACIDS;

EID: 2942532548     PISSN: 00353930     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. G.V. Boyd, J. Chem. Soc., 1958, 1978.
2. H.J. Timpe and A.V. Eltsov, Adv. Heterocycl. Chem., 1983, 33, 185.
3. A.T.Balaban, A. Dinculescu, G.N. Dorofeenco, G.W. Fischer, A.V. Koblik, V.V. Mezheritskii and W. Schroth, Pyrylium Salts. Syntheses, Reactions and Physical Properties, Adv. Het. Chem. Supplement 2, Academic Press, New York, 1982, p.59.
4. K.C. Joshi, P. Singht, S. Taneja, P.J. Cox, R.A. Howie and R.H. Thomson, Tetrahedron, 1982, 38, 2703.
5. R.-P. Godeau, J.-C. Rossi and I. Fouraste, Phytochemistry, 1977, 16, 604.
6. H. Ohashi, T. Tsurushima, T. Ueno and H. Fukami, Agric. Biol. Chem., 1986, 50, 2655; Y.Ge and S. Isoe, Chem. Lett., 1992, 139; F. Abe, H. Okabe, and T. Yamauchi, Chem. Pharm. Bull. (Japan), 1977, 25, 3422.
7. H. Ohashi, T. Tsurushima, T. Ueno and H. Fukami, Agric. Biol. Chem., 1986, 50, 2655; Y.Ge and S. Isoe, Chem. Lett., 1992, 139; F. Abe, H. Okabe, and T. Yamauchi, Chem. Pharm. Bull. (Japan), 1977, 25, 3422.
8. H. Ohashi, T. Tsurushima, T. Ueno and H. Fukami, Agric. Biol. Chem., 1986, 50, 2655; Y.Ge and S. Isoe, Chem. Lett., 1992, 139; F. Abe, H. Okabe, and T. Yamauchi, Chem. Pharm. Bull. (Japan), 1977, 25, 3422.
9. G. Schneider and M. Willems, Arch. Pharm., 1982, 315, 691; G. Schneider and J. Veith, ibid., 1985, 318, 515; R. Braun, H. Dieckmann, M. Machut, C. Echarti and H.R. Maurer, Planta Med., 1986, 446; P.W. Thies, Tetrahedron, 1968, 24, 313.
10. G. Schneider and M. Willems, Arch. Pharm., 1982, 315, 691; G. Schneider and J. Veith, ibid., 1985, 318, 515; R. Braun, H. Dieckmann, M. Machut, C. Echarti and H.R. Maurer, Planta Med., 1986, 446; P.W. Thies, Tetrahedron, 1968, 24, 313.
11. G. Schneider and M. Willems, Arch. Pharm., 1982, 315, 691; G. Schneider and J. Veith, ibid., 1985, 318, 515; R. Braun, H. Dieckmann, M. Machut, C. Echarti and H.R. Maurer, Planta Med., 1986, 446; P.W. Thies, Tetrahedron, 1968, 24, 313.
12. G. Schneider and M. Willems, Arch. Pharm., 1982, 315, 691; G. Schneider and J. Veith, ibid., 1985, 318, 515; R. Braun, H. Dieckmann, M. Machut, C. Echarti and H.R. Maurer, Planta Med., 1986, 446; P.W. Thies, Tetrahedron, 1968, 24, 313.
13. R. Bos, H. Hendricks, J.J. Scheffer and H.J. Woerdenbag, Phytomedicine, 1998, 5, 219.
14. F.E. Koehn, S.P. Gunasekera, D.M. Niel and S.S. Cross, Tetrahedron Lett., 1991, 32, 169.
15. T. Kaempchen, G. Moddelmog, D. Schultz and G. Seitz, Liebigs Ann. Chem., 1988, 855; G. Seitz, G. Moddelmog and J. Hoelzl, Arch. Pharm. 1985, 318, 946.
16. T. Kaempchen, G. Moddelmog, D. Schultz and G. Seitz, Liebigs Ann. Chem., 1988, 855; G. Seitz, G. Moddelmog and J. Hoelzl, Arch. Pharm. 1985, 318, 946.
17. H. Kato, T. Kobayashi, M. Ciobanu, H. Iga, A. Akutsu and A. Kakchi, Chem. Commun., 1996, 1011.
18. M. Christi, N. Bien, G. Bodenschatz, E. Feineis, J. Hegmann, C. Hofmann, S. Mertelmeyer, J. Ostheimer, F. Sammtelben, S. Wehner, E.M. Peters, K. Peters, M. Pfeiffer and D. Stalke, Chem. Commun., 1998, 2387.
19. K. Shimano, Y. Ge, K. Sakaguchi, and S. Isoe, Tetrahedron Lett., 1996, 37, 2253.
20. F. E. Koehn, S.P. Gunasekera, D.N. Niel, and S.S. Cross, Tetrahedron Lett., 1991, 32, 169.
21. J.L. Brayer, J.P. Alazar, and C. Thal, Chem. Commun., 1983, 257.
22. E. Graf and B. Roth, Arch. Pharm. 1982, 315, 733.
23. A. Bianco, M. Guiso, C. Iavarone, R. Marini-Bettolo, and C. Trogolo, Gazz. Chim. Ital., 1976, 106, 733.
24. G. Buechi and J.A. Carlson, J. Am. Chem. Soc., 1969, 91, 6470; 1968, 90, 533; V.E. Rao and T.S.R.A. Anjaneyulu, Indian J. Pharm., 1967, 29, 273.
25. G. Buechi and J.A. Carlson, J. Am. Chem. Soc., 1969, 91, 6470; 1968, 90, 533; V.E. Rao and T.S.R.A. Anjaneyulu, Indian J. Pharm., 1967, 29, 273.
26. G. Buechi and J.A. Carlson, J. Am. Chem. Soc., 1969, 91, 6470; 1968, 90, 533; V.E. Rao and T.S.R.A. Anjaneyulu, Indian J. Pharm., 1967, 29, 273.
27. M.D. Banciu, E.E. Castellano, J. Ellena, I. Haiduc, C. Draghici and A.T. Balaban, New J. Chem., 2001, 25, 1472-1474.