메뉴 건너뛰기




Volumn 63, Issue 18, 2007, Pages 3790-3799

A novel application of the Diels-Alder reaction: nitronaphthalenes as normal electron demand dienophiles

Author keywords

Diels Alder; Dienophiles; Nitronaphthalenes

Indexed keywords

NAPHTHALENE DERIVATIVE; NITRONAPHTHALENE DERIVATIVE; PHENANTHRENE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34047130147     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.054     Document Type: Article
Times cited : (30)

References (78)
  • 41
    • 34047191715 scopus 로고    scopus 로고
    • For preliminary results using naphthalenes 1a-1d in Diels-Alder reactions, see:
  • 47
    • 34047098608 scopus 로고    scopus 로고
    • Della Rosa, C.; Kneeteman, M.; Paredes, E.; Mancini, P. 7th International Electronic Conference on Synthetic Organic Chemistry (ECSOC-7), 2003.
  • 48
    • 34047183534 scopus 로고    scopus 로고
    • Della Rosa, C.; Kneeteman, M.; Mancini, P. 8th International Electronic Conference on Synthetic Organic Chemistry (ECSOC-8), 2004.
  • 49
    • 34047102251 scopus 로고    scopus 로고
    • note
    • Orbital coefficients for 1,3-dinitronaphthalene: C1: 0.457, C2: -0.165, C3: -0.343, C4: 0.599.
  • 54
    • 34047190690 scopus 로고    scopus 로고
    • note
    • LUMO energy (eV): 1a: -2.4679; 1i: -2.6842.
  • 55
    • 34047151125 scopus 로고    scopus 로고
    • note
    • The appearance of the corresponding naphthylamines observed in moderate amounts when employing dienes 5 and 6 with 1a (Table 4, entries 2 and 3), can be kept to a minimum using lower temperatures when possible.
  • 62
    • 34047124597 scopus 로고    scopus 로고
    • note
    • It has not been possible to determine the oxidation derivatives related to the dienes in the reaction crude because of the presence of the corresponding polymerization products.
  • 63
    • 0025946170 scopus 로고
    • As all efforts to isolate any intermediates were unsuccessful, the step where deoxygenation would take place remains unknown. We also believe that a hetero Diels-Alder reaction to the nitro group would be viable taking into account the well referenced cycloadditions using nitroolefins as dienes. (
    • As all efforts to isolate any intermediates were unsuccessful, the step where deoxygenation would take place remains unknown. We also believe that a hetero Diels-Alder reaction to the nitro group would be viable taking into account the well referenced cycloadditions using nitroolefins as dienes. (. Bäckvall J.-E., Karlsson U., and Chinchilla R. Tetrahedron Lett. 32 (1991) 5607-5610
    • (1991) Tetrahedron Lett. , vol.32 , pp. 5607-5610
    • Bäckvall, J.-E.1    Karlsson, U.2    Chinchilla, R.3
  • 66
    • 0033525847 scopus 로고    scopus 로고
    • ). This hypothesis about the parallel N-naphthylpyrroles formation is currently under study in our group and will be the subject of future mechanistical analyses and applications.
    • Avalos M., Babiano R., Cintas P., Highes F.J., Jiménez J.L., Palacios J.C., and Silva M.A. J. Org. Chem. 64 (1999) 1494-1502 ). This hypothesis about the parallel N-naphthylpyrroles formation is currently under study in our group and will be the subject of future mechanistical analyses and applications.
    • (1999) J. Org. Chem. , vol.64 , pp. 1494-1502
    • Avalos, M.1    Babiano, R.2    Cintas, P.3    Highes, F.J.4    Jiménez, J.L.5    Palacios, J.C.6    Silva, M.A.7
  • 67
    • 34047158003 scopus 로고    scopus 로고
    • note
    • LUMO energy (eV): 8: -2.2277; 9a: -1.7047; 9b: -1.6930; 10: -2.7640.
  • 68
    • 34047153169 scopus 로고    scopus 로고
    • Hodgson, H. H.; Mahadevan, A. P.; Ward, E. R. Organic Synthesis; Wiley: New York, NY, 1955; Coll. Vol. III, p 341.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.