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Volumn 130, Issue 48, 2008, Pages 16193-16200

Mixed alkylamido aluminate as a kinetically controlled base

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; ALUMINUM; AROMATIC HYDROCARBONS; KETONES; LITHIUM; ORGANIC COMPOUNDS; PETROLEUM INDUSTRY; THERMOMECHANICAL PULPING PROCESS; ZINC;

EID: 57149111029     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja804749y     Document Type: Article
Times cited : (69)

References (58)
  • 9
    • 33646530550 scopus 로고    scopus 로고
    • Aluminum in Organic Synthesis
    • Yamamoto, H, Oshima, K, Eds, Wiley-VCH: Weinheim, Chapter 6 and references cited therein
    • (a) Saito, S. Aluminum in Organic Synthesis. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 1, Chapter 6 and references cited therein.
    • (2004) Main Group Metals in Organic Synthesis , vol.1
    • Saito, S.1
  • 17
    • 0012397313 scopus 로고
    • For reviews on DoM see: a
    • For reviews on DoM see: (a) Snieckus, V. Chem. Rev. 1990, 90, 879-933.
    • (1990) Chem. Rev , vol.90 , pp. 879-933
    • Snieckus, V.1
  • 24
    • 0001569220 scopus 로고
    • Wilkinson, G, Stone, F. G. A, Abel, E. W, Eds, Pergamon Press: Oxford, Chap. 6 and references cited therein
    • Eisch, J. J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 6, Chap. 6 and references cited therein.
    • (1982) Comprehensive Organometallic Chemistry , vol.6
    • Eisch, J.J.1
  • 40
  • 44
    • 57149106400 scopus 로고    scopus 로고
    • Both Me3Al(TMP)Li and Me3Al(TMP)Li·THF adopt structures analogous to that of i-Bu3Al(TMP)Li·THF. See ref 11b for details
    • 3Al(TMP)Li·THF. See ref 11b for details.
  • 45
    • 57149092494 scopus 로고    scopus 로고
    • We have also identified an energetically plausible intermediate, IM2′, which can be formed by the dissociation of HNMe2 from IM2 for IM2′, ΔErel, 6.9 kcal/mol and ΔGrel, 4.9 kcal/mol, both energies being relative to IM2
    • rel = -4.9 kcal/mol, both energies being relative to IM2).
  • 50
    • 57149086542 scopus 로고    scopus 로고
    • The prediction of accurate Gibbs free energy profiles for reactions in solution remains a challenge for quantum chemical methods, especially in cases in which solvent exchange (association and/or dissociation) takes place at the metal atom. However, favorable error cancelation is expected in the comparison of the similar transition states TS1-3
    • The prediction of accurate Gibbs free energy profiles for reactions in solution remains a challenge for quantum chemical methods, especially in cases in which solvent exchange (association and/or dissociation) takes place at the metal atom. However, favorable error cancelation is expected in the comparison of the similar transition states TS1-3.
  • 51
    • 57149117023 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 52
    • 57149098671 scopus 로고    scopus 로고
    • The structure of 7, reported independently, resulted from the reaction of TMP-aluminate 1 with N,N-diisopropylbenzamide (ref 22). Although not significantly different from ours, the reported structural parameters for 7 have slightly lower esd's.
    • The structure of 7, reported independently, resulted from the reaction of TMP-aluminate 1 with N,N-diisopropylbenzamide (ref 22). Although not significantly different from ours, the reported structural parameters for 7 have slightly lower esd's.


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