Oxidative Anion Metatheses in Diaryliodonium Iodides and Chlorides

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Abstract

Oxidative anion metatheses in the <i>crude</i> title iodides and chlorides produced the corresponding <i>pure</i> hydrogensulfates, nitrates, tetrafluoroborates, triflates, tosylates, as well as bromides and chlorides (only from the iodides) in 54—86% yields. These procedures are easier and shorter than earlier methods. By using modified oxidative metatheses in the title iodides (in the presence of HBr or HCl) it was possible either to isolate, or to detect only, the intermediate dihaloiodates(I), [Ar<sub>2</sub>I]<sup>+</sup>[IX<sub>2</sub>]<sup>−</sup> (X = Br or Cl). A complex Ph<sub>2</sub>I<sup>+</sup>Cl<sup>−</sup>·1/2I<sub>2</sub> was also obtained in 56% yield. Tetraethylammonium iodide was similarly converted into pure tetrafluoroborate or dibromoiodate(I) in 75 and 76% yields, respectively.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 70(1), 219-224, 1997-01-15

    The Chemical Society of Japan

References:  27

  • <no title>

    OLAH G. A.

    Halonium Ions, 1975

    Cited by (4)

  • Halonium Ions

    KOSER G. F.

    The Chemistry of Functional Groups, Supplement D Cha 25, 1983

    Cited by (1)

  • <no title>

    KOSER G. F.

    The Chemistry of Halides, Pseudo-Halides and Azides, Supplement D2 Cha 21

    Cited by (1)

  • <no title>

    VARVOGLIS A.

    The Organic Chemistry of Polycoordinated Iodine, 1992

    Cited by (13)

  • <no title>

    KASUMOV T. M.

    Synthesis 1995, 775

    Cited by (1)

  • <no title>

    VARVOGLIS A.

    Synthesis 1984, 709, 713-717

    Cited by (1)

  • <no title>

    BERINGER F. M.

    J. Am. Chem. Soc. 75, 270, 1953

    Cited by (1)

  • <no title>

    KITAMURA T.

    Synthesis 1994, 147

    Cited by (5)

  • <no title>

    KAZMIERCZAK P.

    Synthesis 1995, 1027

    Cited by (2)

  • <no title>

    SEIKEL M. K.

    Org. Synth. 24, 47, 1994

    Cited by (1)

  • <no title>

    JURD L.

    Aust. J. Sci. Res. 2[A], 595, 1949

    Cited by (1)

  • <no title>

    SUVOROV B. V.

    Okislitel'nye Reaktsii v Organicheskom Sinteze, 173-183, 1978

    Cited by (1)

  • <no title>

    RUDAKOVA N. I.

    Zh. Obshch. Khim. 62, 2290, 1992

    Cited by (1)

  • <no title>

    RUDAKOVA N. I.

    Chem. Abstr. 122, 31241, 1995

    Cited by (1)

  • <no title>

    SCHEIDER H.

    Ger. Patent DE 4442808, 1995

    Cited by (1)

  • <no title>

    SCHEIDER H.

    Chem. Abstr. 124, 29603, 1996

    Cited by (1)

  • <no title>

    FARHAN A. N.

    Communication at a Meeting of the Polish Chemical Society, 1995

    Cited by (1)

  • <no title>

    BERINGER F. M.

    J. Am. Chem. Soc. 60, 141, 1956

    Cited by (1)

  • <no title>

    WHEELER C. M.

    J. Am. Chem. Soc. 77, 2024, 1955

    Cited by (1)

  • <no title>

    BERINGER F. M.

    Iodine Abstr. Rev. 3, 70, 1956

    Cited by (2)

  • <no title>

    ZEFIROV N. S.

    Synthesis 1993, 1209

    Cited by (1)

  • <no title>

    ZEFIROV N. S.

    Synthesis 1995, 1359

    Cited by (1)

  • <no title>

    Dictionary of Organic Compounds, 1996

    Cited by (4)

  • Organic Polyvalent Iodine Compounds

    STANG P. J.

    Chem. Rev. 96, 1123, 1996

    DOI  Cited by (2)

  • <no title>

    FORSTER M. O.

    J. Chem. Soc. 101, 382, 1912

    DOI  Cited by (1)

  • <no title>

    CHATTAWAY F. D.

    J. Chem. Soc. 123, 654, 1923

    DOI  Cited by (1)

  • <no title>

    DEKTAR J. L.

    J. Org. Chem. 55, 639, 1990

    DOI  Cited by (2)

Codes

  • NII Article ID (NAID)
    10008915302
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • NDL Article ID
    4142533
  • NDL Source Classification
    ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-B35
  • Data Source
    CJP  NDL  J-STAGE 
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