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Volumn 76, Issue 13, 2011, Pages 5404-5412

A short desymmetrization protocol for the coordination environment in bis-salphen scaffolds

Author keywords

[No Author keywords available]

Indexed keywords

COORDINATION ENVIRONMENT; DESYM-METRIZATION; DIIMINES; IMINE BONDS; LEWIS ACIDIC; SUBSTITUTION PATTERNS; TEMPLATE EFFECTS;

EID: 79959672608     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2008065     Document Type: Article
Times cited : (16)

References (39)
  • 26
    • 79959672047 scopus 로고    scopus 로고
    • In this work, we demonstrate that symmetrical bis-salphens can be converted in two steps into bis-salphens with each salphen unit being nonsymmetrical, i.e., a formal desymmetrization in each salphen coordination pocket.
    • In this work, we demonstrate that symmetrical bis-salphens can be converted in two steps into bis-salphens with each salphen unit being nonsymmetrical, i.e., a formal desymmetrization in each salphen coordination pocket.
  • 31
    • 79959657340 scopus 로고    scopus 로고
    • Note that time may be a decisive parameter as the intermediate species contain imine bonds that are potentially susceptible toward undesired hydrolysis and/or scrambling; this may have affected the overall isolated yield of 12 and 13.
    • Note that time may be a decisive parameter as the intermediate species contain imine bonds that are potentially susceptible toward undesired hydrolysis and/or scrambling; this may have affected the overall isolated yield of 12 and 13.
  • 33
    • 70749149667 scopus 로고    scopus 로고
    • Note that a stepwise templating approach was previously used for the synthesis of nonsymmetrical, heterobimetallic salphens. See
    • Note that a stepwise templating approach was previously used for the synthesis of nonsymmetrical, heterobimetallic salphens. See: Castilla, A. M.; Curreli, S.; Martínez Belmonte, M.; Escudero-Adán, E. C.; Benet-Buchholz, J.; Kleij, A. W. Org. Lett. 2009, 11, 5218
    • (2009) Org. Lett. , vol.11 , pp. 5218
    • Castilla, A.M.1    Curreli, S.2    Martínez Belmonte, M.3    Escudero-Adán, E.C.4    Benet-Buchholz, J.5    Kleij, A.W.6
  • 34
    • 66249123127 scopus 로고    scopus 로고
    • 4OAc (see the Supporting Information). The incorporation of OAc donors in these highly Lewis acidic Zn complexes is not surprising taking into account a previous communication from our group. Here we demonstrated that acetate anions may form bridges between two Zn(II) centers, thereby creating supramolecular structures. See:;;, The presence of acetate donors provokes broadening of the NMR signals; the recrystallization of these essentially pure isolated materials was carried out to display sharp NMR patterns to show unequivocally the dissymmetric nature of these compounds.
    • 4OAc (see the Supporting Information). The incorporation of OAc donors in these highly Lewis acidic Zn complexes is not surprising taking into account a previous communication from our group. Here we demonstrated that acetate anions may form bridges between two Zn(II) centers, thereby creating supramolecular structures. See: Wezenberg, S. J.; Escudero-Adán, E. C.; Benet-Buchholz, J.; Kleij, A. W. Chem.-Eur. J. 2009, 15, 5695 The presence of acetate donors provokes broadening of the NMR signals; the recrystallization of these essentially pure isolated materials was carried out to display sharp NMR patterns to show unequivocally the dissymmetric nature of these compounds.
    • (2009) Chem.-Eur. J. , vol.15 , pp. 5695
    • Wezenberg, S.J.1    Escudero-Adán, E.C.2    Benet-Buchholz, J.3    Kleij, A.W.4
  • 35
    • 79959678000 scopus 로고    scopus 로고
    • The LanL2DZ basis set and effective core potential were used for the Zn atoms, and the split-valence 6-31G(d,p) basis set was applied for all other atoms.
    • The LanL2DZ basis set and effective core potential were used for the Zn atoms, and the split-valence 6-31G(d,p) basis set was applied for all other atoms.
  • 36
    • 79959683879 scopus 로고    scopus 로고
    • The original reactions were performed at 0.012 M, whereas more concentrated reactions were carried out at 0.016, 0.019, and 0.024 M giving isolated yields of 11 in the range 12-35%.
    • The original reactions were performed at 0.012 M, whereas more concentrated reactions were carried out at 0.016, 0.019, and 0.024 M giving isolated yields of 11 in the range 12-35%.
  • 38
    • 79959683569 scopus 로고    scopus 로고
    • SHELXTL Crystallographic System Ver. 5.10, Bruker AXS, Inc.: Madison, WI.
    • Sheldrick, G. M. SHELXTL Crystallographic System Ver. 5.10, Bruker AXS, Inc.: Madison, WI, 1998.
    • (1998)
    • Sheldrick, G.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.