Reactivity of N-phenyl-1-aza-2-cyano-1,3-butadienes in the Diels-Alder reaction

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3715-3728

  Sisti, Nicholas J ^c   Motorina, Irina A ^c   Tran Huu Dau, Marie Elise ^c   Riche, Claude ^c   Fowler, Frank W ^a   Grierson, David S ^b  

^a STONY BROOK UNIVERSITY   (United States)

^b CNRS   (France)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000129707     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9520607     Document Type: Article

References (68)

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21. In general, <3-5% of the N-triflyl product is formed under the experimental conditions employed. However, it is important to separate completely this contaminant from the product 2-cyano-1-azadienes, as in instances where trace quantities of this material remain extensive decomposition is observed in cycloaddition reactions with ethyl vinyl ether and methyl acrylate: Parly, F.; Motorina, I.; Fowler, F. W.; Grierson, D. S., manuscript in preparation.
22. 6c good yields (75%) of cycloadduct 6 were obtained on heating azadiene 4 with ethyl vinyl ether for shorter periods (26 h), but under these conditions the azadiene 4 was not totally consumed.
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24. C-Hax by 10 ± 1 Hz. An only 5 Hz difference compared to a compound of known stereochemistry or the near identity of this coupling for compounds believed to be of opposite stereochemistry strongly indicates that such systems are not conformationally stable. For relevant applications of this technique, see: (a) Boch, K.; Pederson, C. J. Chem. Soc., Perkin Trans. 2 1974, 293. (b) Takeuchi, Y.; Chivers, P. J.; Crabb, T. A. J. Chem. Soc., Chem. Commun. 1974, 210. (c) Bonin, M.; Chiaroni, A.; Riche, C.; Beloeil, J.-C.; Grierson, D. S. J. Org. Chem. 1987, 52, 382. (d) Reference 5d.
25. C-Hax by 10 ± 1 Hz. An only 5 Hz difference compared to a compound of known stereochemistry or the near identity of this coupling for compounds believed to be of opposite stereochemistry strongly indicates that such systems are not conformationally stable. For relevant applications of this technique, see: (a) Boch, K.; Pederson, C. J. Chem. Soc., Perkin Trans. 2 1974, 293. (b) Takeuchi, Y.; Chivers, P. J.; Crabb, T. A. J. Chem. Soc., Chem. Commun. 1974, 210. (c) Bonin, M.; Chiaroni, A.; Riche, C.; Beloeil, J.-C.; Grierson, D. S. J. Org. Chem. 1987, 52, 382. (d) Reference 5d.
26. C-Hax by 10 ± 1 Hz. An only 5 Hz difference compared to a compound of known stereochemistry or the near identity of this coupling for compounds believed to be of opposite stereochemistry strongly indicates that such systems are not conformationally stable. For relevant applications of this technique, see: (a) Boch, K.; Pederson, C. J. Chem. Soc., Perkin Trans. 2 1974, 293. (b) Takeuchi, Y.; Chivers, P. J.; Crabb, T. A. J. Chem. Soc., Chem. Commun. 1974, 210. (c) Bonin, M.; Chiaroni, A.; Riche, C.; Beloeil, J.-C.; Grierson, D. S. J. Org. Chem. 1987, 52, 382. (d) Reference 5d.
27. The authors have deposited atomic coordinates for the structures 11, 18, and 29 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.
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31. 3OD). However, no appreciable variations in signal heights (integration) were detected. On heating the NMR probe to 100 °C the H-4 absorption for the minor component in 27 was observed to broaden, and additional signals appeared both in the olefinic region (δ 5.23-5.56 and 6.36) and for a third methyl group (δ 1.89). However, assignment of these signals to enamine 28 and to the cis 4-methyl isomer of 27 can only be considered tentatively, since treatment of the mixture with acid did not result in the expected dissapearance of the new olefinic signals (28 → 27).
32. For a related papers on the propensity of N-aryl-3-cyano-substituted 1-azadienes to react with both electron rich and electron deficient dienophiles; see: (a) Sakamoto, M.; Nozaka, A.; Shimamoto, M.; Ozaki, H.; Suzuki, Y.; Yoshioka, S.; Nagano, M.; Okamura, K.; Date, T.; Tamura, O. Chem. Pharm. Bull. 1994, 42, 1367. (b) Sakamoto, M.; Nozaka, A.; Shimamoto, M.; Ozaki, H., Suzuki, Y.; Yoshioka, S.; Nagano, M.; Okamura, K.; Date, T.; Tamura, O. J. Chem. Soc., Perkin Trans. 1 1995, 1759.
33. For a related papers on the propensity of N-aryl-3-cyano-substituted 1-azadienes to react with both electron rich and electron deficient dienophiles; see: (a) Sakamoto, M.; Nozaka, A.; Shimamoto, M.; Ozaki, H.; Suzuki, Y.; Yoshioka, S.; Nagano, M.; Okamura, K.; Date, T.; Tamura, O. Chem. Pharm. Bull. 1994, 42, 1367. (b) Sakamoto, M.; Nozaka, A.; Shimamoto, M.; Ozaki, H., Suzuki, Y.; Yoshioka, S.; Nagano, M.; Okamura, K.; Date, T.; Tamura, O. J. Chem. Soc., Perkin Trans. 1 1995, 1759.
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54. 37-39
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