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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 3-4
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Original Articles

Study of the Influence of Ultrasound and Aqueous Solvent on the Diels-Alder Reaction: The Case of Cyclopentadiene and Acetamidoacrylates

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Pages 473-476 | Received 30 Jun 1988, Published online: 23 Oct 2006

References

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  • Rahm , A. and Jenner , G. 1985 . L'actualité Chimique , : 41 Matsumoto, K.; Hashimoto, S.; Ikemi, Y.; Otani, S. Heterocycles, 1986, 24, 1835.
  • Breslow , R. , Maitra , U. and Rideout , D. 1983 . Tetrahedron Lett. , 24 1901;Breslow, R.; Maitra, U. ibid. 1984, 25, 1239; Rideout, D. C.; Breslow, R. J. Am. Chem. Soc., 1980, 102, 7816.
  • Grieco , P. A. , Galatsis , P. and Spohn , R. F. 1986 . Tetrahedron , 42 : 2847 Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc., 1985, 107, 1768 and references therein.
  • Sternbach , D. D. and Rossana , D. M. 1982 . J. Am. Chem. Soc. , 104 : 5853
  • Horikawa , H. , Nishitani , T. , Iwasaki , T. , Mushika , Y. , Inove , I. and Miyoshi , M. 1980 . Tetrahedron Lett. , 21 : 4101
  • endo-2-acetamido-exo-2-benzyloxycarbonylbicyclo [2,2,1]hept-5-ene, 2a 300. MHz 1H nmr (CDCl3) δ : 7.35 (m, 5H, Ph), 6.31 (bs, 1H, NH), 6.43 (d, 1H, = CH), 6.13 (m, 1H, = CH), 5.17 (s, 2H, CH2-Ph), 3.37 (m, 1H, CH), 2.93 (m, 1H, CH), 2.69 (dd, 1H, CH), 1.89 (s, 3H, CH3), 1.80 (d, 1H, CH), 1.53 (m, 1H, CH), 1.25 (dd, 1H, CH). exo-2-acetamido-endo-2-benzyloxycarbonylbicyclo [2,2.1]hept-5-ene, 2 a 300. MHz 1H nmr (CDCl3) δ : 7.32 (m, 5H, Ph), 6.31 (m, 1H, = CH), 6.22 (bs, 1H, NH), 5.73 (m, 1H, = CH), 5.06 (d, 2H, CH2-Ph), 2.95 (m, 2H, CH), 2.36 (dd, 1H, CH), 1.96 (s, 3H, CH3), 1.80–1.73 (m, 2H, CH), 1.57 (m, 1H, CH). 2b exo, 2b endo see reference 7.
  • Bueno , M. P. , Cativiela , C. , Finol , C. , Mayoral , J. A. and Jaime. , C. 1987 . Can. J. Chem. , 65 : 2182
  • Most of the olefin 1 disappears at the end of the reaction (1H nmr of the crude) but, contrary to some authors, we have not used this as a criterium of the completeness of the Diels-Alder reaction. It is clear that a significant part of the acetamidoacrylate does not yield the cycloadduct.

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