The retro-nazarov reaction

Journal of the American Chemical Society

Volumn 124, Issue 48, 2002, Pages 14328-14329

  Harmata, Michael ^a   Lee, Dong Reyoul ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTADIENE DERIVATIVE; TRIFLUOROETHANOL;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; RETRO NAZAROV REACTION;

EID: 0037021555     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028729q     Document Type: Article

References (6)

1. Harmata, M.; Barnes, C. L.; Brackley, J.; Bohnert, G.; Kirchhoefer, P.; Kürti, L.; Rashatasakhon, P. J. Org. Chem. 2001, 66, 5232-5236.
2. Prepared by bromination/dehydrobromination of the corresponding enone. For synthesis of the enone, see: Schwartz, J.; Loots, M. J.; Kosugi, H. J. Am. Chem. Soc. 1980, 102, 1333-1340.
3. Schottenberger, H.; Buchmeiser, M. R.; Angleimer, H.; Wurst, K.; Herber, R. H. J. Organomet. Chem. 2000, 605, 174-183.
4. The Nazarov cyclization is a powerful method for five-membered ring formation that has been extensively studied and applied in synthesis. For reviews and recent studies of the process, see: (a) Habermas, K. L.; Denmark, S. E.; Jones, T. K. Org. React. 1994, 45, 1-158. (b) Giese, S.; Kastrup, L.; Stiens, D.; West, F. G. Angew. Chem., Int. Ed. 2000, 39, 1970-1973 and references therein.
5. The Nazarov cyclization is a powerful method for five-membered ring formation that has been extensively studied and applied in synthesis. For reviews and recent studies of the process, see: (a) Habermas, K. L.; Denmark, S. E.; Jones, T. K. Org. React. 1994, 45, 1-158. (b) Giese, S.; Kastrup, L.; Stiens, D.; West, F. G. Angew. Chem., Int. Ed. 2000, 39, 1970-1973 and references therein.
6. Kallel, E. A.; Houk, K. N. J. Org. Chem. 1989, 54, 6006-6008.