Effect of cyclopentenone annelation on a cycloheptatriene - Norcaradiene equilibrium

Recueil des Travaux Chimiques des Pays-Bas-Journal of the Royal Netherlands

Volumn 115, Issue 2, 1996, Pages 149-150

  Oda, Mitsunori ^a   Horiguchi, Hidemasa ^a   Masaki, Yoshimi ^a   Sakamoto, Yukinari ^a   Kuroda, Shigeyasu ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748848098     PISSN: 01650513     EISSN: None     Source Type: Journal    
DOI: 10.1002/recl.19961150209     Document Type: Article

References (19)

1. F. R. Jensen and L. A. Smith, J. Am. Chem. Soc., 86, 956(1964).
2. For a recent paper see, S. Kohmoto, T. Funabashi, N. Nakayama, T. Nishio, I. Iida, K. Kishikawa, M. Yamamoto, and K. Yamada, J. Org. Chem., 58, 4764 (1993)
3. For reviews see, (a) G. Maier, Angew. Chem., Int. Ed. Engl., 6, 402(1967);
4. (b) K. Takeuchi, J. Synth. Org. Chem., Jpn., 30, 40(1985).
5. (a) W. von E. Doering and M. J. Goldstein, Tetrahedron, 5, 53(1959);
6. (b) M. Balci and B. Atasoy, Tetrahedron Lett., 25, 4033(1984);
7. (c) K. A. Burdett, F. L. Shenton, D. H. Yates, and J. S. Swenton, Tetrahedron, 30, 2057 (1974).
8. F.-G. Klärner, E. K. G. Schmidt, and M.A. Rahman, Angew. Chem., Int. Ed. Engl., 21, 138(1982).
9. A. Saba, Tetrahedron Lett., 32, 4657(1990).
10. (a) R. Hoffmann, Tetrahedron Lett., 2907(1970);
11. (b) H. Günther, Tetrahedron Lett., 5173(1970).
12. In this paper we use a trivial name, dihydroazulenone, for 4-8, because numbering of these compounds according to the IUPAC rule is confusing for understanding double bond positions.
13. A. Costantino, G. Linstrumelle, and S. Julia, Bull. Soc. Chim. Fr., 907(1970).
14. (a) L. T. Scott, J. Chem. Soc., Chem. Commun., 882 ( 1973);
15. (b) L. T. Scott, M. A. Minton, and M. A. Kirms, J. Am. Chem. Soc., 102, 6311(1980).
16. 3 solution with tetramethylsilane as internal standard.
17. It was pointed out that 8 exists entirely in the CHT form in reference (6).
18. Since real proton chemical shifts for pure state of the CHT and NCD forms have not been revealed, expected values were used instead; the value(2.52ppm) of seven-membered ring methylene protons of 7 for that of the pure CHT forms and the average chemical shift (0.48ppm) of the cyclopropane methylene protons of 2,3-benznorcaradiene for that of the pure NCD forms.
19. For study of a CHT-NCD equilibrium by IR and Raman spectra see, E. Ciganek, J. Am. Chem. Soc., 93, 2207(1971).