Sterospecific Actolysis of threo- and erythro-2-Aryl-2-[1-methylthio)ethl]oxiranes

Access this Article

Search this Article

Author(s)

Abstract

<i>Threo</i>-2-aryl-2-[1-(methylthio)ethyl]oxiranes (<b>1a</b>—<b>d</b>) were reacted with acetic acid to give two types of unexpected ring-opening products, <i>threo</i>-1-acetoxy-2-aryl-3-methylthio-2-butanols (<b>4a</b>—<b>d</b>) and mono-<i>O</i>-acetyl derivatives of <i>threo</i>-2-aryl-2-methylthio-1,3-butanediol (<b>5a</b>—<b>d</b> and <b>6a</b>—<b>d</b>). On the other hand, <i>erythro</i>-2-aryl-2-[1-(methylthio)ethyl]oxiranes (<b>2a</b>—<b>d</b>) gave <i>erythro</i>-1-acetoxy-2-aryl-3-methylthio-2-butanols (<b>7a</b>—<b>d</b>) and mono-<i>O</i>-acetyl derivatives of <i>erythro</i>-2-aryl-2-methylthio-1,3-butanediol (<b>8a</b>—<b>d</b> and <b>9a</b>—<b>d</b>). It is suggested that these products are generated from thiiranium ionic intermediates, because they all completely retain the relative configuration of the starting oxiranes.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 68(6), 1731-1737, 1995-06-15

    The Chemical Society of Japan

References:  13

  • <no title>

    SAJI I.

    8th Medicinal Chemistry Symposium, 9-12, 1986

    Cited by (2)

  • <no title>

    SAJI I.

    European Patent 178533, 1986

    Cited by (2)

  • <no title>

    SAJI I.

    Chem. Abstr. 105, 35613r, 1986

    Cited by (1)

  • <no title>

    SAJI I.

    Bull. Chem. Soc. Jpn. 67, 1427, 1994

    Cited by (3)

  • <no title>

    TASAKA A.

    Chem. Pharm. Bull. 41, 1035, 1993

    Cited by (4)

  • <no title>

    KONOSU T.

    Chem. Pharm. Bull. 39, 2241, 1991

    Cited by (2)

  • <no title>

    OGATA M.

    Eur. J. Med. Chem. 24, 137, 1989

    Cited by (1)

  • <no title>

    YAMAKAWA K.

    Chem. Pharm. Bull. 27, 953, 1979

    Cited by (1)

  • <no title>

    DERZHINSKII A. R.

    Izu. Akad. Nauk SSSR 11, 2652, 1984

    Cited by (1)

  • <no title>

    GILL D. M.

    J. Chem. Soc. Perkin Trans. 1 1993, 1371

    Cited by (1)

  • <no title>

    TANAKA Y.

    European Patent 552974, 1993

    Cited by (1)

  • <no title>

    TANAKA Y.

    Chem. Abstr. 120, 134499, 1993

    Cited by (1)

  • <no title>

    LADIKA M.

    Tetrahedron Lett. 27, 1703, 1986

    DOI  Cited by (1)

Codes

  • NII Article ID (NAID)
    10008891075
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • Data Source
    CJP  J-STAGE 
Page Top