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Volumn 127, Issue 36, 2005, Pages 12472-12473

Interrupted Nazarov cyclization on silica gel

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; SILICA GEL;

EID: 24744438218     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja053393g     Document Type: Article
Times cited : (59)

References (24)
  • 1
    • 0001992172 scopus 로고
    • Paquette, L. A., Ed.; John Wiley & Sons: New York.
    • For reviews of the Nazarov reaction, see: (a) Habermas, K. L.; Denmark, S.; Jones, T. K. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York. 1994; Vol. 45, pp 1-158.
    • (1994) Organic Reactions , vol.45 , pp. 1-158
    • Habermas, K.L.1    Denmark, S.2    Jones, T.K.3
  • 2
  • 8
    • 0033610446 scopus 로고    scopus 로고
    • We have discussed the origin of the strong preference for formation of the Z exocyclic double bond isomer: Hu, H.; Smith, D.; Cramer, R. E.; Tius, M. A. J. Am. Chem. Soc. 1999, 121, 9895-9896.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9895-9896
    • Hu, H.1    Smith, D.2    Cramer, R.E.3    Tius, M.A.4
  • 9
    • 24744461463 scopus 로고    scopus 로고
    • note
    • Silica gel was activated by heating under vacuum at 160 °C for 16 h.
  • 11
    • 6444231809 scopus 로고    scopus 로고
    • For an example of reactions taking place on silica gel in the presence of solvent, see: (b) Wipf, P.; Aoyama, Y.; Benedum, T. E. Org. Lett. 2004, 6, 3593-3595.
    • (2004) Org. Lett. , vol.6 , pp. 3593-3595
    • Wipf, P.1    Aoyama, Y.2    Benedum, T.E.3
  • 13
    • 24744461559 scopus 로고    scopus 로고
    • note
    • The choice of methyl ethers for this work was to avoid the alternative reaction pathway, the rapid termination process that involves cleavage of methoxymethyl ethers.
  • 20
    • 24744466610 scopus 로고    scopus 로고
    • note
    • A small number of experiments using solid amines did not lead to satisfactory results.
  • 22
    • 24744455775 scopus 로고    scopus 로고
    • note
    • The methyl protons in 11 showed a positive nOe with the ortho phenyl protons, and the benzylic proton showed a nOe with some of the cyclohexyl protons.
  • 23
    • 24744448776 scopus 로고    scopus 로고
    • note
    • 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.