Isotope effects for lewis acid catalyzed Diels-Alder reactions. The experimental transition state

Tetrahedron Letters

Volumn 40, Issue 32, 1999, Pages 5817-5821

  Singleton, Daniel A ^a   Merrigan, Steven R ^a   Beno, Brett R ^b   Houk, K N ^b  

^a TEXAS A AND M UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Catalysis; Diels Alder reactions; Isotope effects; Transition states

Indexed keywords

ACROLEIN; ACRYLIC ACID ETHYL ESTER; ISOPRENE; KETONE DERIVATIVE;

ACCURACY; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS;

BETULACEAE;

EID: 0033529832     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01148-X     Document Type: Article

References (18)

1. Thompson, H. W.; Melillo, D. G. J. Am. Chem. Soc. 1970, 92, 3218.
2. Houk, K. N.; Strozier, R. W. J. Am. Chem. Soc. 1973, 95, 4094.
3. Yamabe, S.; Dai, T.; Minato, T. J. Am. Chem. Soc. 1995, 117, 10994.
4. García, J. I.; Martínez-Merino, V.; Mayoral, J. A.; Salvatella, L. J. Am. Chem. Soc. 1998, 120, 2415.
5. (a) Beno, B. R.; Houk, K. N.; Singleton, D. A. J. Am. Chem. Soc. 1996, 118, 9984.
6. (b) Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 3385.
7. (c) Frantz, D. E.; Singleton, D. A.; Snyder, J. P. J. Am. Chem. Soc. 1997, 119, 3383.
8. (d) DelMonte, A. J.; Haller, J.; Houk, K. N.; Sharpless, K. B.; Singleton, D. A.; Straßner, T.; Thomas, A. A. J. Am. Chem. Soc. 1997, 119, 9907.
9. Singleton, D. A.; Thomas, A. A. J. Am. Chem. Soc. 1995, 117, 9357.
10. This reaction is highly exothermic. It was necessary to add the catalyst last in small portions over several hours.
11. 2H KIE.
12. Birney, D. M.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 4127.
13. Singleton, D. A. J. Am. Chem. Soc. 1992, 114, 6563.
14. (a) Bigeleisen, J.; Mayer, M. G. J. Chem. Phys. 1947, 75, 261.
15. (b) Wolfsberg, M. Acc. Chem. Res. 1972, 5, 225.
16. The calculations used the program QUIVER (Saunders, M.; Laidig, K. E.; Wolfsberg, M. J. Am. Chem. Soc. 1989, 111, 8989) with Becke3LYP frequencies scaled by 0.9614. (Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502).
17. The calculations used the program QUIVER (Saunders, M.; Laidig, K. E.; Wolfsberg, M. J. Am. Chem. Soc. 1989, 111, 8989) with Becke3LYP frequencies scaled by 0.9614. (Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502).
18. Bell, R. P. The Tunnel Effect in Chemistry; Chapman and Hall: London, 1980; pp. 60-63.