Diels-Alder Reactions of 5-Alkyl-1,3-cyclopentadienes

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7272-7277

  Letourneau, Johnathon E ^a   Wellman, Mark A ^a   Burnell, D Jean ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000978921     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9707949     Document Type: Article

References (34)

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13. Mironov, V. A.; Fadeeva, T. M.; Akhrem, A. A. Dokl. Akad. Nauk SSSR 1967, 174, 852-855.
14. Burnell, D. J.; Valenta, Z. J. Chem. Soc., Chem. Commun. 1985, 1247-1248. An earlier study reported a 3.5:1 ratio for the anti and syn adducts, respectively, with maleic anhydride: Mironov, V. A.; Fadeeva, T. M.; Pashegorova, V. S.; Stepanyants, A. U.; Akhrem, A. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1968, 423-425.
15. Burnell, D. J.; Valenta, Z. J. Chem. Soc., Chem. Commun. 1985, 1247-1248. An earlier study reported a 3.5:1 ratio for the anti and syn adducts, respectively, with maleic anhydride: Mironov, V. A.; Fadeeva, T. M.; Pashegorova, V. S.; Stepanyants, A. U.; Akhrem, A. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1968, 423-425.
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28. "Syn" and "anti" addition is defined with dienes 3, 7, and 44 as relative to the ethyl, the methoxymethyl, or the hydroxymethyl on C-5.
29. Diene 41 has twice as many reactive faces as 3.
30. (a) Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; John Wiley & Sons: New York, 1989; pp 255-261 and references therein.
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34. Atomic coordinates for the X-ray structure have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.