Endo Preference in the Diels-Alder Cycloaddition of Butadiene and Maleic Anhydride

Journal of Organic Chemistry

Volumn 47, Issue 21, 1982, Pages 4170-4171

  Stephenson, L M ^a   Smith, D E ^a   Current, S P ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001741863     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00142a035     Document Type: Article

References (14)

1. Alder, K.; Stein, G. Angew. Chem. 1937, 50, 510.
2. Martin, J. G.; Hill, R. K. Chem. Rev. 1961, 61, 537–562. This is a comprehensive review of stereochemical features of the Diels-Alder reaction.
3. Wassermann, A. J. Chem. Soc. 1935, 825, 1511; 1936, 432;
4. Trans. Faraday Soc. 1939, 35, 841;
5. “Diels-Alder Reactions”; Elsevier: New York, 1965.
6. Woodward, R. B.; Baer, H. J. Am. Chem. Soc. 1944, 66, 645.
7. Woodward, R. B.; Katz, T. J. Tetrahedron 1959, 5, 70.
8. Hoffmann, R.; Woodward, R. B. J. Am. Chem. Soc. 1965, 87, 4388.
9. Woodward, R. B.; Hoffmann, R. Angew. Chem. Int. Ed. Engl. 1969, 8, 781.
10. Herndon, W. C.; Hall, L. H. Tetrahedron Lett. 1967, 3095.
11. Stephenson, L. M.; Gemmer, R. V.; Current, S. P. J. Org. Chem. 1977, 42, 212.
12. Stephenson, L. M.; Gemmer, R. V.; Current, S. J. Am. Chem. Soc. 1975, 97, 5909.
13. Graham, C. R.; Stephenson, L. M. J. Am. Chem. Soc. 1977, 99, 7098.
14. Most recently see Houk, K. N. Tetrahedron Lett. 1970, 2621. By comparing cyclopentene to cyclopentadiene as dienophiles, Houk concludes that the second double bond stabilizes the endo transition state by 2.5–5.0 kcal/mol. This was ascribed to a secondary orbital interaction.