A Willgerodt-Kindler Type Selenation of Dihalomethane Derivatives, Chloroform, and Sodium Trichloroacetate by Treating with a Base, Elemental Selenium, and an Amine

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Abstract

Treatment of dihalomethane derivatives, chloroform, or sodium trichloroacetate with elemental selenium in the presence of NaH and an excess amount of an amine gave the corresponding selenoamides, selenoureas, and bis(selenocarbamoyl) triselenides in modest yields. These products were afforded from reactive intermediates related to “selenocarbonyl halides” and “selenophosgenoids” generated by the reaction of dichloromethanide ions and trichloromethanide ion with <i>N</i>-alkylated aminopolyselenide species (R<sub>2</sub>N–(Se)<sub><i>n</i></sub><sup>−</sup>).

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 69(8), 2235-2242, 1996-08-15

    The Chemical Society of Japan

References:  38

  • <no title>

    COLLARD-CHARON C.

    Bull. Soc. Chim. Belg. 72, 304, 1963

    Cited by (1)

  • <no title>

    RAE I. D.

    Int. J. Sulfur Chem. 8, 519, 1976

    Cited by (2)

  • <no title>

    VOSS J.

    Liebigs Ann. Chem. 1979, 1931

    Cited by (2)

  • <no title>

    STELIOU K.

    J. Am. Chem. Soc. 104, 3104, 1982

    Cited by (4)

  • <no title>

    SEGI M.

    Synlett 1991, 105

    Cited by (10)

  • <no title>

    SEGI M.

    Tetrahedron Lett. 33, 7865, 1992

    Cited by (8)

  • <no title>

    SHIMADA K.

    Chem. Lett. 1990, 1403

    Cited by (3)

  • <no title>

    TAKIKAWA Y.

    Bull.Chem.Soc.Jpn. 67, 876, 1994

    Cited by (5)

  • <no title>

    OKUMA K.

    Chem. Lett. 1992, 131

    Cited by (2)

  • <no title>

    NAKAYAMA J.

    Chem. Lett. 1994, 77

    Cited by (1)

  • <no title>

    HOCK R.

    Chem. Ber. 126, 1895, 1993

    Cited by (4)

  • <no title>

    NAKAYAMA J.

    Tetrahedron Lett. 24, 2585, 1983

    Cited by (4)

  • <no title>

    CARMACK M.

    Organic Reactions 3, 83, 1946

    Cited by (1)

  • <no title>

    TAKIKAWA Y.

    Chem. Lett. 1994, 2105

    Cited by (1)

  • <no title>

    SEKIYA M.

    Yuki Gosei Kagaku Kyokaishi 41, 395, 1983

    Cited by (2)

  • <no title>

    PARHAM W. E.

    Organic Reactions 13, 55, 1963

    Cited by (2)

  • <no title>

    HENRIKSEN L.

    Synthesis 1982, 773

    Cited by (2)

  • <no title>

    OGAWA A.

    Bull. Chem. Soc. Jpn. 58, 1448, 1985

    Cited by (3)

  • <no title>

    KOCHHAR K. S.

    Tetrahedron Lett. 24, 1323, 1983

    Cited by (5)

  • <no title>

    SHIMADA K.

    Chem. Lett. 1994, 1743

    Cited by (6)

  • <no title>

    ERKER G.

    J. Am. Chem. Soc. 110, 624, 1988

    Cited by (6)

  • <no title>

    SEGI M.

    Tetrahedron Lett. 32, 7427, 1991

    Cited by (4)

  • <no title>

    GLADYSZ J. A.

    J. Org. Chem. 43, 1204, 1978

    Cited by (5)

  • <no title>

    HENRIKSEN L.

    Synthesis 1982, 771

    Cited by (2)

  • <no title>

    BARNARD D.

    J. Chem. Phys. 1961, 2922

    Cited by (1)

  • <no title>

    MOSS R. A.

    J. Org. Chem. 34, 2220, 1969

    Cited by (1)

  • <no title>

    MOSS R. A.

    J. Am. Chem. Soc. 96, 5632, 1974

    Cited by (2)

  • <no title>

    PADWA A.

    J. Org. Chem. 34, 2728, 1969

    Cited by (2)

  • <no title>

    SATO R.

    Phosphorus and Sulfur 7, 289, 1979

    Cited by (1)

  • <no title>

    SASAKI Y.

    Can. J. Chem. 49, 283, 1971

    Cited by (1)

  • <no title>

    MILLIGAN B.

    J. Chem. Soc. 1961, 1194

    Cited by (1)

  • <no title>

    GAUTHERON B.

    J. Am. Chem. Soc. 107, 5579, 1985

    Cited by (3)

  • <no title>

    DARMADI A.

    Z. Naturforsch., B: Anorg. Chem., Org. Chem. 36B, 1261, 1981

    Cited by (1)

  • <no title>

    ISHII A.

    Bull. Chem. Soc. Jpn. 61, 861, 1988

    Cited by (8)

  • <no title>

    MCEWEN W. L.

    Org. Synth., Coll. 2, 133, 1950

    Cited by (1)

  • <no title>

    GRAHAM W. H.

    J. Am. Chem. Soc. 87, 4396, 1965

    Cited by (2)

  • <no title>

    JENSEN K. A.

    Acta Chem. Scand. 20, 597, 1966

    DOI  Cited by (8)

  • <no title>

    ABELMAN M. M.

    Tetrahedron Lett. 32, 7389, 1991

    DOI  Cited by (2)

Codes

  • NII Article ID (NAID)
    10008907116
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • NDL Article ID
    4060542
  • 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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