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Volumn 48, Issue 46, 2009, Pages 8721-8724

Hindered ureas as masked isocyanates: Facile carbamoylation of nucleophiles under neutral conditions

Author keywords

Carbamoylation; Isocyanates; Proton switch; Reaction mechanisms; Urea solvolysis

Indexed keywords

CARBAMOYLATION; FASTER RATES; IN-SITU; ISOCYANATES; NEUTRAL CONDITIONS; NUCLEOPHILIC SUBSTITUTIONS; REACTION MECHANISMS;

EID: 70350578527     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200904435     Document Type: Article
Times cited : (99)

References (28)
  • 1
    • 0000757084 scopus 로고    scopus 로고
    • For selected examples of the generally forcing conditions needed for the cleavage of urea, see: a) J. Akester, J. Cui, G. Fraenkel, J. Org. Chem. 1997, 62, 431;
    • (1997) J. Org. Chem. , vol.62 , pp. 431
    • Akester, J.1    Cui, J.2    Fraenkel, G.3
  • 12
    • 70350612093 scopus 로고    scopus 로고
    • note
    • -1 higher in energy, thereby predicting a slower methanolysis of 3 c than 3 a by the addition/elimination pathway, which is in contrast to our observation.
  • 23
    • 70350617540 scopus 로고    scopus 로고
    • Amides, carbamates, and tetrasubstituted ureas fail to react under methanolysis conditions (see the Supporting Informaition)
    • Amides, carbamates, and tetrasubstituted ureas fail to react under methanolysis conditions (see the Supporting Informaition).
  • 27
    • 37049075899 scopus 로고
    • CCDC 749529 (for compound 3c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC 749529 (for compound 3c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif. Compound 3a is a known compound: R. J. Lewis, P. Camilleri, A. J. Kirby, C. A. Marby, A. A. Slawin, D. J. Williams, J. Chem. Soc. Perkin Trans. 2, 1991, 1625.
    • (1991) J. Chem. Soc. Perkin Trans. , vol.2 , pp. 1625
    • Lewis, R.J.1    Camilleri, P.2    Kirby, A.J.3    Marby, C.A.4    Slawin, A.A.5    Williams, D.J.6
  • 28
    • 0004845505 scopus 로고
    • N′N′-dialkyl ureas of 2,6-xylidine undergo slow dissociation in anisóle (40-140°C) to generate equilibrium mixtures of N-(2,6dimethylphenyl)isocyanate and the corresponding dialkylamine: J. C. Stowell, S. J. Padegimas, J. Org. Chem. 1974, 39, 2448.
    • (1974) J. Org. Chem. , vol.39 , pp. 2448
    • Stowell, J.C.1    Padegimas, S.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.