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Volumn 124, Issue 47, 2002, Pages 14147-14155

Metal ion-catalyzed Diels-Alder and hydride transfer reactions. Catalysis of metal ions in the electron-transfer step

Author keywords

[No Author keywords available]

Indexed keywords

DIELS-ALDER REACTIONS; ELECTRON TRANSFER;

EID: 0037184498     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja026417h     Document Type: Article
Times cited : (88)

References (90)
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    • + has been discussed extensively. (a) Grieco, P. A.; Nunes, J. J.; Gaul. M. D. J. Am. Chem. Soc. 1990, 112, 4595. (b) Waldmann, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1306. (c) Smith, D. A.; Houk, K. N. Tetrahedron Lett. 1991, 32, 1549. (d) Forman, M. A.; Dailey, W, P. J. Am. Chem. Soc. 1991, 113, 2761. (e) Desimoni, G.; Faita, G.; Righetti, P. P.; Tacconi, G. Tetrahedron 1991, 47, 8399. (f) Pagni, R. M.; Kabalka, G. W.; Bains, S.; Plesco, M.; Wilson, J.; Bartmess, J. J. Org. Chem. 1993, 58, 3130. (g) Jiao, H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1995, 117, 11529. (h) Kumar, A. J. Org. Chem. 1994, 59, 4612. (i) Kumar, A.; Pawar, S. S. J. Org. Chem. 2001, 66, 7646.
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    • note
    • n+-promoted" electron transfer. In the case of the Diels - Alder reactions (eq 1), the metal ion acts as a real catalyst.
  • 76
    • 2242434792 scopus 로고    scopus 로고
    • note
    • -1, see Table 1).
  • 78
    • 2242432970 scopus 로고    scopus 로고
    • note
    • 30
  • 81
    • 2242494830 scopus 로고    scopus 로고
    • note
    • 2 value at 333 K (Table 2) is smaller than the corresponding value at 298 K (Table 1) because of the negative value of enthalphy of the complex formation.
  • 82
    • 2242448349 scopus 로고    scopus 로고
    • note
    • cat values in Figure 5c are larger than those in Figure 5b because of the higher reaction temperature (333 K in Figure 5c as compared to 298 K in Figure 5b).
  • 87
    • 2242462573 scopus 로고    scopus 로고
    • note
    • 39 analogous structures for the p-fluoranil radical anion - metal ion complex are unavailable.
  • 89
    • 2242475172 scopus 로고    scopus 로고
    • note
    • The spin density on the fluorine atom is determined mainly by the direct spin delocalization due to the hyperconjugation which induces a positive spin density in contrast with the spin polarization which induces a negative spin density.
  • 90
    • 2242495728 scopus 로고    scopus 로고
    • note
    • 2+ complex (Scheme 3).


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