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Volumn 131, Issue 7, 2009, Pages 2452-2453

Highly selective monomethylation of primary amines through host-guest product sequestration

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM SALT; ASSOCIATION CONSTANT; CAVITAND; COMPLETE CONTROL; H-BONDING; HOST-GUEST; INTERMEDIATE REACTIONS; ION-DIPOLE; MONOMETHYLATION; N-METHYLATION; PHOSPHONATE; PRIMARY AMINES; REACTION MEDIUM; SYNERGISTIC COMBINATIONS;

EID: 67749143923     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja809614y     Document Type: Article
Times cited : (63)

References (37)
  • 1
    • 0141472615 scopus 로고
    • Patai, S, Eds, Interscience: London, Chapter 2, pp
    • (a) Gibson, M. S. The Chemistry of the Amino Group; Patai, S., Eds.; Interscience: London, 1968; Chapter 2, pp 45-62.
    • (1968) The Chemistry of the Amino Group , pp. 45-62
    • Gibson, M.S.1
  • 3
    • 67849115242 scopus 로고    scopus 로고
    • Salvatore, R. N.; Yoon, C. H.; Jung, K. W. Tetrahedron 2001, 57, 77857811.
    • (c) Salvatore, R. N.; Yoon, C. H.; Jung, K. W. Tetrahedron 2001, 57, 77857811.
  • 12
    • 0141768469 scopus 로고    scopus 로고
    • For alternative N-monomethylation methodologies see: a
    • For alternative N-monomethylation methodologies see: (a) Selva, M.; Tundo, P. Tetrahedron Lett. 2003, 44, 8139-8142.
    • (2003) Tetrahedron Lett , vol.44 , pp. 8139-8142
    • Selva, M.1    Tundo, P.2
  • 25
    • 67849123389 scopus 로고    scopus 로고
    • In a standard amine alkylation reaction, even if the electrophile is the limiting reagent, the equilibrium between the protonated product and the starting amine is rapid enough to result in a complex mixture
    • In a standard amine alkylation reaction, even if the electrophile is the limiting reagent, the equilibrium between the protonated product and the starting amine is rapid enough to result in a complex mixture.
  • 30
    • 67849089686 scopus 로고    scopus 로고
    • The reaction is conducted by adding 1 equiv of sequestrating agent and 3 equiv of methyl iodide to a solution of n-butylamine (0.035 M) in chloroform at room temperature.
    • The reaction is conducted by adding 1 equiv of sequestrating agent and 3 equiv of methyl iodide to a solution of n-butylamine (0.035 M) in chloroform at room temperature.
  • 34
    • 53849133462 scopus 로고    scopus 로고
    • For an alternative, catalytic monoarylation protocol see
    • For an alternative, catalytic monoarylation protocol see: Fors, B. P.; Watson, D. A.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 1355213554.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 1355213554
    • Fors, B.P.1    Watson, D.A.2    Biscoe, M.R.3    Buchwald, S.L.4
  • 35
    • 67849087824 scopus 로고    scopus 로고
    • In the case of cyclohexylamine, total conversion to the corresponding ammonium salt was incomplete after 16 h at room temperature, indicating the influence of steric effects on the reaction rate
    • In the case of cyclohexylamine, total conversion to the corresponding ammonium salt was incomplete after 16 h at room temperature, indicating the influence of steric effects on the reaction rate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.