Conversion of (sp^3)C-F Bonds of Alkyl Fluorides to (sp^3)C-Heteroatom (Heteroatom = I, SR, SeR, TeR) Bonds by the Use of Magnesium Reagents Having Heteroatom Substituents

この論文にアクセスする

この論文をさがす

著者

    • BEGUM Shameem Ara
    • Department of Applied Chemistry, Graduate School of Engineering, Osaka University
    • TERAO Jun
    • Science and Technology Center for Atoms, Molecules and Ions Control, Graduate School of Engineering, Osaka University
    • KAMBE Nobuaki
    • Department of Applied Chemistry, Graduate School of Engineering, Osaka University

抄録

A convenient method for conversion of (sp<SUP>3</SUP>)C–F bonds to (sp<SUP>3</SUP>)C–Z (Z = I, SR, SeR, TeR) bonds has been developed. The reaction proceeds at room temperature using magnesium salts (Z–MgX). S<SUB>N</SUB>2 mechanism for substitiution of <I>primary</I> alkyl fluorides with MgI<SUB>2</SUB> in ether was supported by the inversion of the stereochemistry of the carbon connecting to F.

収録刊行物

  • Chemistry letters

    Chemistry letters 36(1), 196-197, 2007-01-05

    The Chemical Society of Japan

参考文献:  18件中 1-18件 を表示

  • <no title>

    HIYAMA T. ed.

    Organofluorine Compounds Chemistry and Applications, 2000

    被引用文献1件

  • <no title>

    FUCHIBE K.

    J. Am. Chem. Soc. 128, 1434, 2006

    被引用文献1件

  • <no title>

    HIRANO K.

    Tetrahedron Lett. 45, 2555, 2004

    被引用文献1件

  • <no title>

    TERAO J.

    Angew. Chem., Int. Ed. 43, 6180, 2004

    被引用文献1件

  • <no title>

    TERAO J.

    J. Am. Chem. Soc. 127, 3656, 2005

    被引用文献1件

  • <no title>

    TERAO J.

    Chem. Commun., 2007

    被引用文献1件

  • <no title>

    KIRRMANN A.

    C. R. Seances Acad. Sci., Ser. C 268, 547, 1969

    被引用文献1件

  • <no title>

    HATAKEYAMA T.

    J. Am. Chem. Soc. 127, 14192, 2005

    DOI 被引用文献1件

  • <no title>

    KOSMRLJ B.

    Tetrahedron Lett. 36, 7921, 1995

    被引用文献1件

  • <no title>

    OOI T.

    Tetrahedron Lett. 38, 5679, 1997

    被引用文献2件

  • <no title>

    TOSHIMA K.

    Carbohydr. Res. 327, 15, 2000

    被引用文献2件

  • <no title>

    FILIPPO J. S. Jr.

    J. Org. Chem. 40, 3295, 1975

    被引用文献1件

  • <no title>

    OLAH G. A.

    J. Org. Chem. 46, 3727, 1981

    被引用文献2件

  • <no title>

    NAMAVARI M.

    J. Fluorine Chem. 72, 89, 1995

    被引用文献2件

  • <no title>

    TERAO J.

    J. Am. Chem. Soc. 125, 5646, 2003

    被引用文献10件

  • <no title>

    KRAFT B. M.

    J. Am. Chem. Soc. 123, 10973, 2001

    被引用文献1件

  • <no title>

    NEWCOMB M.

    J. Org. Chem. 64, 1225, 1999

    被引用文献1件

  • <no title>

    HERRERA R. P.

    Tetrahedron Lett. 44, 1309, 2003

    被引用文献1件

各種コード

  • NII論文ID(NAID)
    10018664141
  • NII書誌ID(NCID)
    AA00603318
  • 本文言語コード
    ENG
  • 資料種別
    SHO
  • ISSN
    03667022
  • データ提供元
    CJP書誌  J-STAGE 
ページトップへ