Alkali-metal-mediated zincation of polycyclic aromatic hydrocarbons: Synthesis and structures of mono- and dizincated naphthalenes

被引：57
|
作者：
Clegg, William
Dale, Sophie H.
Hevia, Eva
Hogg, Lorna M.
Honeyman, Gordon W.
Mulvey, Robert E. [1 ]
O'Hara, Charles T.
机构：
[1] Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland
[2] Univ Newcastle, Sch Nat Sci Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 39期
关键词：
alkali metals; crystal structures; metalation; polycyclic aromatic hydrocarbons; zinc;
D O I：
10.1002/anie.200602288
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Figure Presented) Zinc twice: Naphthalene is attacked and doubly deprotonated at the 2,6-position by a synergic sodium zincate base to generate a centrosymmetric dizincated molecule. The approach of alkali-metal-mediated zincation can effect dimetalation as well as monometalation of polycyclic aromatic hydrocarbons, thus providing access to new zincated naphthalenes that are inaccessible directly through mainstream organozinc reagents. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：6548 / 6550
页数：3
相关论文
共 50 条
  • [1] Alkali-metal-mediated zincation of anisole: Synthesis and structures of three instructive ortho-zincated complexes
    Clegg, William
    Dale, Sophie H.
    Drummond, Allison M.
    Hevia, Eva
    Honeyman, Gordon W.
    Mulvey, Robert E.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) : 7434 - 7435
  • [2] Alkali-metal-mediated zincation of anisole: Synthesis and structures of three instructive ortho-zincated complexes
    Clegg, William
    Dale, Sophie H.
    Drummond, Allison M.
    Hevia, Eva
    Honeyman, Gordon W.
    Mulvey, Robert E.
    Journal of the American Chemical Society, 2006, 128 (23): : 7434 - 7435
  • [3] Concerning the Structures of Alkali-Metal-Mediated ortho Zincation of Benzamides and Phenyl O-Carbamate
    Balloch, Liam
    Kennedy, Alan R.
    Mulvey, Robert E.
    Rantanen, Toni
    Robertson, Stuart D.
    Snieckus, Victor
    ORGANOMETALLICS, 2011, 30 (01) : 145 - 152
  • [4] Directed meta-metalation using alkali-metal-mediated zincation
    Armstrong, David R.
    Clegg, William
    Dale, Sophie H.
    Hevia, Eva
    Hogg, Lorna M.
    Honeyman, Gordon W.
    Mulvey, Robert E.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (23) : 3775 - 3778
  • [5] Alkali-Metal-Mediated Manganation(II) of Naphthalenes: Constructing Metal la-Anthracene and Metalla-Phenanthrene Structures
    Blair, Victoria L.
    Clegg, William
    Mulvey, Robert E.
    Russo, Luca
    INORGANIC CHEMISTRY, 2009, 48 (18) : 8863 - 8870
  • [6] Mono- and polycyclic aromatic polymers - synthesis and properties
    Maier, S.
    Davey, A.P.
    Drury, A.
    Byrne, H.J.
    Blau, W.
    Synthetic Metals, 1999, 101 (01): : 31 - 32
  • [7] Mono- and polycyclic aromatic polymers - synthesis and properties
    Maier, S
    Davey, AP
    Drury, A
    Byrne, HJ
    Blau, W
    SYNTHETIC METALS, 1999, 101 (1-3) : 31 - 32
  • [8] Pre-metalation structural insights into the use of alkali-metal-mediated zincation for directed ortho-metalation of a tertiary aromatic amide
    Clegg, W
    Dale, SH
    Hevia, E
    Honeyman, GW
    Mulvey, RE
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (15) : 2370 - 2374
  • [9] Comparison of the reactions of mono- and polycyclic aromatic hydrocarbons with oxygen atoms
    Freichs, H.
    Tappe, M.
    Wagner, H.Gg.
    Berichte der Bunsengesellschaft fuer Physikalische Chemie, 1990, 94 (11):
  • [10] Post-metalation structural insights into the use of alkali-metal-mediated zincation for directed ortho-metalation of a tertiary aromatic amide
    Clegg, William
    Dale, Sophie H.
    Harrington, Ross W.
    Hevla, Eva
    Honeyman, Gordon W.
    Mulvey, Robert E.
    Angewandte Chemie - International Edition, 2006, 45 (15) : 2374 - 2377
12345