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Volumn 11, Issue 1, 2009, Pages 245-247

Addition of N-heterocyclic carbenes to imines: phenoxide assisted deprotonation of an imidazolium moiety and generation of Breslow intermediates derived from imines

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; IMINE; METHANE; OXIDE; PROTON;

EID: 59649118413     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802572n     Document Type: Article
Times cited : (42)

References (31)
  • 1
  • 2
    • 64349087788 scopus 로고    scopus 로고
    • N-Heterocyclic Carbenes (NHC) in Transition Met al. Catalysis; Glorius, F., Ed.; Topic in Organomet al.lic Chemistry, 28; Springer-Verlag: Berlin, 2006.
    • (b) N-Heterocyclic Carbenes (NHC) in Transition Met al. Catalysis; Glorius, F., Ed.; Topic in Organomet al.lic Chemistry, Vol. 28; Springer-Verlag: Berlin, 2006.
  • 7
    • 1942472372 scopus 로고    scopus 로고
    • 2nd ed, Wiley-VCH: Weinheim, For recent examples where met al. NHC intermediates are directly implicated in bicyclic heterocycle synthesis see
    • (a) Eicher, T.; Hauptnamm, S. The Chemistry of Heterocycles: Structure, Reactions, Synthesis, and Applications, 2nd ed.; Wiley-VCH: Weinheim, 2003. For recent examples where met al. NHC intermediates are directly implicated in bicyclic heterocycle synthesis see:
    • (2003) The Chemistry of Heterocycles: Structure, Reactions, Synthesis, and Applications
    • Eicher, T.1    Hauptnamm, S.2
  • 20
    • 64349123982 scopus 로고    scopus 로고
    • Reversible reactions between an NHC and activated ALtosylarylimines have been described in refs 5a and 5c.
    • Reversible reactions between an NHC and activated ALtosylarylimines have been described in refs 5a and 5c.
  • 21
    • 0142165772 scopus 로고    scopus 로고
    • Bonnet, L. G.; Douthwaite, R. E.; Kariuki, B. M. Organomet al.lics 2003, 22, 4187.
    • (a) Bonnet, L. G.; Douthwaite, R. E.; Kariuki, B. M. Organomet al.lics 2003, 22, 4187.
  • 22
    • 38949109588 scopus 로고    scopus 로고
    • Dyson, G.; Frison, J. C.; Simonovic, S.; Whitwood, A. C.; Douthwaite, R. E. Organomet al.lics 2008, 27, 281.
    • (b) Dyson, G.; Frison, J. C.; Simonovic, S.; Whitwood, A. C.; Douthwaite, R. E. Organomet al.lics 2008, 27, 281.
  • 29
    • 64349115942 scopus 로고    scopus 로고
    • For a structurally characterized phenoxide-imidazolium adduct and discussion of proton location, see ref 8
    • For a structurally characterized phenoxide-imidazolium adduct and discussion of proton location, see ref 8.
  • 30
    • 64349108012 scopus 로고    scopus 로고
    • A related imidazolium-amide has been characterized for an N-tosylarylimine in ref 5c.
    • A related imidazolium-amide has been characterized for an N-tosylarylimine in ref 5c.
  • 31
    • 64349121451 scopus 로고    scopus 로고
    • a's of related phenols: phenol (9.99), 4-tert-butylphenol (10.23), and 4-nitrophenol (7.15) ; from Lange's Handbook of Chemistry, 14th ed; McGraw-Hill: New York, 1992; Table 8.8.
    • a's of related phenols: phenol (9.99), 4-tert-butylphenol (10.23), and 4-nitrophenol (7.15) ; from Lange's Handbook of Chemistry, 14th ed; McGraw-Hill: New York, 1992; Table 8.8.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.