Vinyl benzenes as dienes in mild solid-phase Diels-Alder reactions

Journal of Organic Chemistry

Volumn 65, Issue 8, 2000, Pages 2555-2559

  Sun, Sengen ^a   Turchi, Ignatius J ^a   Xu, Dawei ^a   Murray, William V ^a  

^a R W JOHNSON PHARMACEUTICAL RES I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; DEMETHYLATION; HEATING; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034697123     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991956z     Document Type: Article

References (15)

1. (a) Wagner-Jauregg, T. Synthesis 1980, 769.
2. (b) Klemm, L. H.; McGuire, T. M.; Gopinath, K. W. J. Org. Chem. 1976, 41, 2571.
3. Diment, J. A.; Ritchie, E.; Taylor, W. C. Aust. J. Chem. 1969, 22, 1721.
4. Stranix, B. R.; Darling G. D. J. Org. Chem. 1997, 62, 9001.
5. (a) Schlessinger, R. H.; Bergstrom C. P. Tetrahedron Lett. 1996, 37, 2133.
6. (b) Tietze, L. F.; Hippe, T.; Steinmetz, A. Synlett 1996, 1043.
7. Heerding, D. A.; Takata, D. T.; Kwon, C.; Huffman, W. F.; Samanen, J. Tetrhedron Lett. 1998, 39, 6815.
8. Ball, C. P.; Barrett, A. G. M.; Commercon, A.; Compere, D.; Kuhn, C.; Roberts, R. S.; Smith, M. L., Venier, O. Chem. Commun. 1998, 2019.
9. (e) Wendeborn, S.; De Mesmaeker, A.; Brill, W. K.-D. Synlett 1998, 865.
10. Murray, W. V.; Sun, S.; Turchi, I. J.; Brown, F. K.; Guathier, A. D. J. Org. Chem. 1999, 64, 5930.
11. Sun, S.; Murray, W. V. J. Org. Chem. 1999, 64, 5941.
12. The progress of the reactions was monitored by cleavage of the product from solid support.
13. Gaussian 98, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; and Pople, J. A.; Gaussian, Inc., Pittsburgh, PA, 1998.
14. SPARTAN (v. 5.0.3), Wavefunction, Inc., Irvine, CA.
15. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.