Stereochemical labeling at natural abundance. Stereochemistry, isotope effects, and mechanism of the Diels-Alder reaction of hexachlorocyclopentadiene with ethyl vinyl ether

Tetrahedron Letters

Volumn 40, Issue 4, 1999, Pages 639-642

  Singleton, Daniel A ^a   Merrigan, Steven R ^a   Thomas, Allen A ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ETHER DERIVATIVE; ISOTOPE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; KINETICS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

BETULACEAE;

EID: 0033593307     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02508-8     Document Type: Article

References (24)

1. For a review, see: Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 779.
2. (a) Sustmann, R.; Tappanchai, S.; Bandmann, H. J. Am. Chem. Soc. 1996, 118, 12555.
3. (b) Sustmann, R.; Sicking, W. J. Am. Chem. Soc. 1996, 118, 12555.
4. (c) Leung, S. -W.; Singleton, D. A. J. Org. Chem. 1997, 62, 1955.
5. Mark, V. J. Org. Chem. 1974, 39, 3179.
6. Lambert, J. B.; McLaughlin, C. D.; Mark, V. Tetrahedron 1976, 32, 2075.
7. (a) Kukalenko, S. S.; Mel'nikov, N, N, Zh. Obshch. Khim. 1958, 28, 157.
8. (b) A few drops of pyridine were added to the reaction mixtures to avoid acid-catalyzed processes.
9. (c) For stereochemical and NMR assignments in related systems, see: Williamson, K. L. J. Am. Chem. Soc. 1963, 85, 516.
10. (a) Martin, G. J.; Martin, M. L. Tetrahedron Lett. 1981, 22, 3525.
11. (b) For reviews, see: Martin, G. J.; Guillou, C.; Martin, M. L.; Cabanis, M. T.; Tep, Y.; Aerny, J. J. Agric. Food Chem. 1988, 36, 316. Martin, G. J.; Martin, M. L.; Martin, Y. -L. Bull. Magn. Reson. 1996, 18, 9.
12. (b) For reviews, see: Martin, G. J.; Guillou, C.; Martin, M. L.; Cabanis, M. T.; Tep, Y.; Aerny, J. J. Agric. Food Chem. 1988, 36, 316. Martin, G. J.; Martin, M. L.; Martin, Y. -L. Bull. Magn. Reson. 1996, 18, 9.
13. 2H NMR integrations.
14. (a) The excess deuterium trans in 2 would drop rapidly with incomplete stereospecificity. For example, if the stereochemistry of each isotopomer were retained in the product to the extent of only 95%, the excess deuterium trans in 2 would only be 27.5%, outside of experimental error.
15. (b) In principle the excess deuterium trans in 2 could arise from a completely non-stereospecific process exhibiting a large isotope effect on product formation, but this seems very unlikely.
16. Singleton, D. A.; Thomas, A. A. J. Am. Chem. Soc. 1995, 117, 9357.
17. (a) Storer, J. W.; Raimondi, L.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 9675.
18. (b) Olson, L. P.; Niwayama, S.; Yoo, H. Y.; Houk, K. N.; Harris, N. J.; Gajewski, J. J. J. Am. Chem. Soc. 1996, 118, 886-892, and references therein.
19. Gajewski, J. J.; Peterson, K. B.; Kagel, J. R.; Huang, Y. C. J. J. Am. Chem. Soc. 1989, 111, 9078.
20. (a) Beno, B. R.; Houk, K. N.; Singleton, D. A. J. Am. Chem. Soc. 1996, 118, 9984-5.
21. (b) Becke3LYP frequencies were scaled by 0.9614. Tunneling corrections were applied using the one-dimensional infinite parabolic barrier model.
22. D's have been adjusted by 1/0.977.
23. Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 9285. 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, 9907-9908.
24. Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 9285. 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, 9907-9908.