Free radical mediated construction of small ring compounds: The double annulation of bicyclo[3.1.0]hex-2-enes

Tetrahedron Letters

Volumn 38, Issue 23, 1997, Pages 4165-4168

  Ferjančić, Zorana ^a   Saičić, Radomir N ^a   Čeković, Živorad ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; FREE RADICAL;

ARTICLE; CYCLIZATION; DECOMPOSITION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0342617556     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00811-3     Document Type: Article

References (20)

1. For comprehensive reviews see: a) Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K.J. and Trach, F. in: Organic Reactions , Ed. Paquette, L.A. et al., J. Wiley&Sons, 1996, Vol. 48, p. 301-855;
2. b) Curran, D.P. in: Comprehensive Organic Synthesis, Editors: Trost, B. and Fleming, I., Pergamon Press, 1991, Vol. 4, p.715-831
3. Effio, A.; Griller, D.; Ingold, K.U.; Beckwith, A.L.J.; Serelis, A.K. J. Am. Chem. Soc. 1980, 102, 1734-1736
4. Maillard, B.; Forrest, D.; Ingold, K.U. J. Am. Chem. Soc. 1976, 98, 7024-7026
5. For the examples of free radical cyclopropanation see: a) Srikrishna, A.; Sharma, G.V.R. J. Chem. Soc. Perkin Trans. 1, 1997, 177-181;
6. b) Journet, M.; Malacria, M. J. Org. Chem. 1994, 59, 718-719;
7. c) Weng, W.W.; Luh, T.L. J. Org. Chem. 1993, 58, 5574-5575;
8. d) Zhang, W.; Dowd, P. Tetrahedron Lett. 1992, 33, 7307-7310;
9. e) Warner, C.R.; Strunk, R.J.; Kuivila, H.G. J. Org. Chem. 1966, 31, 3381-3384;
10. f) Halgren, T.A.; Howden, M.B.H.; Medof, M.E.; Roberts, J.D. J. Am. Chem. Soc. 1967, 89, 3051-3052
11. Čeković, Ž.; Saičić, R.N. Tetrahedron Lett. 1990, 31, 6085-6088
12. Denis, R.C.; Gravel, D. Tetrahedron Lett. 1994, 35, 4531-4534
13. Saičić, R.N.; Čeković, Ž. Tetrahedron 1992, 41, 8975-8992
14. Grieco, P.A.; Wang, C.L.J. J. Chem. Soc. Chem. Communications 1975, 714-715
15. +), 165, 164, 137, 105
16. a) Beckwith, A.L.J.; O'Shea, D.M. Tetrahedron Lett. 1986, 27, 4525-4528;
17. b) Stork, G.; Mook, R. Tetrahedron Lett. 1986, 27, 4529-4532
18. According to the notation introduced by Curran: Curran, D.P. Synlett 1991, 63-72
19. For a previous synthetic application of this principle see: Saičić, R.N.; Čeković, Ž. Tetrahedron Lett. 1994, 35, 7845-7848
20. Corey, E.J.; Cheng, X.-M. The Logic of Chemical Synthesis, John Wiley&Sons, 1989, p. 28-30