Base catalyzed pentacyclo[4.3.0.02,4.03,8.05,7]nonan-9-one (norsnoutanone) → tricyclo[3.2.1.02,7]octanetransformation: A higher order fragmentation?

Tetrahedron Letters

Volumn 37, Issue 15, 1996, Pages 2655-2658

  Mehta, Goverdhan ^a   Ravikrishna, Ch ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029868094     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00353-X     Document Type: Article

References (14)

1. Prinzbach, H.; Eberbach, W.; Van Veh, G. Angew. Chem. Int. Ed. Engl. 1965, 4, 436; Bloch, R.; Leyendecker, F.; Toshima, N. Tetrahedron Lett. 1973, 1025; Miller, R.D.; Dolce, D.L.; Tetrahedron Lett. 1973, 4403; Erden, I. Chem. Lett. 1981, 263.
2. Prinzbach, H.; Eberbach, W.; Van Veh, G. Angew. Chem. Int. Ed. Engl. 1965, 4, 436; Bloch, R.; Leyendecker, F.; Toshima, N. Tetrahedron Lett. 1973, 1025; Miller, R.D.; Dolce, D.L.; Tetrahedron Lett. 1973, 4403; Erden, I. Chem. Lett. 1981, 263.
3. Prinzbach, H.; Eberbach, W.; Van Veh, G. Angew. Chem. Int. Ed. Engl. 1965, 4, 436; Bloch, R.; Leyendecker, F.; Toshima, N. Tetrahedron Lett. 1973, 1025; Miller, R.D.; Dolce, D.L.; Tetrahedron Lett. 1973, 4403; Erden, I. Chem. Lett. 1981, 263.
4. Prinzbach, H.; Eberbach, W.; Van Veh, G. Angew. Chem. Int. Ed. Engl. 1965, 4, 436; Bloch, R.; Leyendecker, F.; Toshima, N. Tetrahedron Lett. 1973, 1025; Miller, R.D.; Dolce, D.L.; Tetrahedron Lett. 1973, 4403; Erden, I. Chem. Lett. 1981, 263.
5. For examples of base catalyzed Haller-Bauer type cleavage of non-enolizable ketones, see, Gassman, P.G.; Lumb, J.T.; Zalar, F.V. J. Am. Chem. Soc. 1967, 89, 946; Mehta, G.; Praveen, M. J. Chem. Soc. Chem. Commun. 1993, 1573.
6. For examples of base catalyzed Haller-Bauer type cleavage of non-enolizable ketones, see, Gassman, P.G.; Lumb, J.T.; Zalar, F.V. J. Am. Chem. Soc. 1967, 89, 946; Mehta, G.; Praveen, M. J. Chem. Soc. Chem. Commun. 1993, 1573.
7. 5,7]nonan-9-one (norsnoutanone) has been reported but it furnishes bicyclo[3.2.1]octa-2,6-diene derivative via the involvement of a bishomocyclopentadienyl anion intermediate. Dauben, W.G.; Twieg, R.J. Tetrahedron Lett., 1974, 531. However, in the substituted derivatives 2a-c, the electron withdrawing substituent suppresses this pathway and only fragmentation products are obtained.
8. (a) Paquette, L.A. Synthesis, 1975, 347;
9. (b) Paquette, L.A.; Ward, J.S.; Boggs, R.A.; Farnham, W.B. J. Am. Chem. Soc. 1975, 97, 1101;
10. (c) Mehta, G.; Ravikrishna, Ch.; Ravikumar, K. J. Chem. Soc. Chem. Commun. 1994, 2321.
11. 3): δ 175.9, 64.1, 51.9, 41.2, 39.5, 32.1, 30.0(2C), 25.0, 24.2, 23.4.
12. 2,7]octene derivatives, see: Huebner, C.F.; Donoghue, E.; Dorfman, L.; Stuber, F..A.; Danieli, N.; Wenkert, E. Tetrahedron Lett., 1966, 1185.
13. Grob, C.A.; Schiess, P.W. Angew. Chem. Int. Engl. 1967, 6, 1.
14. For an example of decarboxylative higher order fragmentation, see: Sternbach, D.; Shibuya, M.; Jaisli, F.; Bonetti, M.; Eschenmoser, A. Angew. Chem. Int. Ed. Engl. 1979, 18, 634.