Silver-Promoted Reactions of Bicyclo[3.2.1]octadiene Derivatives

Organic Letters

Volumn 4, Issue 12, 2002, Pages 1997-2000

  Orugunty, Ravi S ^a   Wright, Dennis L ^a   Battiste, Merle A ^a   Abboud, Khalil A ^a  

^a University of Florida ^*  (United States)

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ARTICLE;

EID: 0346559945     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0258740     Document Type: Article

References (15)

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2. Wright, D. L.; Whitehead, C. R.; Sessions, E. H.; Ghiriviga, I.; Frey, D. A. Org. Lett. 1999, 1, 1535.
3. Wright, D. L.; Usher, L. C.; Estrella-Jimenez, M. Org. Lett. 2001, 3, 4275.
4. For excellent reviews, see: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (b) Noyori, R.; Hayakawa, Y. Tetrahedron 1985, 41, 5879. (d) Rigby, J. H.; Pigge, F. C. In Organic Reactions Paquette, L. A., Ed.; Wiley and Sons: New York, 1997; Vol. 51, p 351.
5. For excellent reviews, see: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (b) Noyori, R.; Hayakawa, Y. Tetrahedron 1985, 41, 5879. (d) Rigby, J. H.; Pigge, F. C. In Organic Reactions Paquette, L. A., Ed.; Wiley and Sons: New York, 1997; Vol. 51, p 351.
6. For excellent reviews, see: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (b) Noyori, R.; Hayakawa, Y. Tetrahedron 1985, 41, 5879. (d) Rigby, J. H.; Pigge, F. C. In Organic Reactions Paquette, L. A., Ed.; Wiley and Sons: New York, 1997; Vol. 51, p 351.
7. Tobey, S. W.; West, R. J. Am. Chem. Soc. 1966, 88, 2481.
8. (a) Apeloig, Y.; Arad, D.; Kapon, M.; Wallerstein, M. Tetrahedron Lett. 1987, 28, 5917.
9. (b) Müller, P.; Bernardinelli, G.; Pfyffer, J.; Rodriguez, D.; Schaller, J.-P. Helv. Chim. Acta 1988, 71, 544.
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11. Warner, P. M.; Lu, S.-L.; Myers, E.; DeHaven, P. W.; Jacobsen, R. A. J. Am. Chem. Soc. 1977, 99, 5102.
12. Olah, G. A.; Kuhn, S. J.; Flood, S. H.; Hardie, B. A. Chem. Ind. 1957, 50.
13. GC-MS and crude NMR data indicated that the products of the reaction contained multiple aryl rings and a cleaved oxo-bridge.
14. Compound B has not been observed in any of the reactions.
15. AM1 calculations indicate that the exo and endo adducts from anisole only differ by 0.88 kcal/mol in favor of the exo arene.