Stereospecific interconversion between cis and trans 2,3-epoxysulfides

被引:0
|
作者
Hirai, A [1 ]
Tonooka, T [1 ]
Wakatsuki, K [1 ]
Tanino, K [1 ]
Miyashita, M [1 ]
机构
[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan
关键词
bromohydrins; epoxidation; isomerization; nucleophilic substitution; synthetic methods;
D O I
10.1002/1521-3773(20020301)41:5<819::AID-ANIE819>3.0.CO;2-J
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A double inversion of configuration and episulfonium ion intermediates are at the heart of a method for the stereospecific interconversion between cis and trans 2,3-epoxysulfides (see scheme). This method can be used in the stereoselective synthesis of epoxides.
引用
收藏
页码:819 / +
页数:4
相关论文
共 50 条
  • [21] Switchable trans-cis interconversion of an amphiphilic anthracene trimer
    Iwasa, Junji
    Ono, Kosuke
    Fujita, Makoto
    Akita, Munetaka
    Yoshizawa, Michito
    CHEMICAL COMMUNICATIONS, 2009, (38) : 5746 - 5748
  • [22] Cadmium cyclam complexes:: Interconversion of cis and trans configurations and fixation of CO2
    Liang, XY
    Parkinson, JA
    Parsons, S
    Weishäupl, M
    Sadler, PJ
    INORGANIC CHEMISTRY, 2002, 41 (17) : 4539 - 4547
  • [23] Trans-cis octahedral interconversion pathway in diorganotin compounds
    Rossi, M
    Caruso, F
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (08) : 1535 - 1543
  • [24] CIS TO TRANS INTERCONVERSION OF CYCLIC ALPHA-HYDROXY EPOXIDES
    ROBERTS, MR
    PARSONS, WH
    SCHLESSINGER, RH
    JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (20): : 3970 - 3972
  • [25] Cis-trans isomerization of dimethyl 2,3-dibromofumarate
    Vo, Timothy H.
    Korlacki, Rafal
    Sinitskii, Alexander
    RSC ADVANCES, 2022, 12 (50) : 32471 - 32474
  • [27] A NEW STEREOSPECIFIC SYNTHESIS OF 2,3-TRANS-3,4-TRANS-FLAVAN-3,4-DIOL
    SHARMA, TC
    VERMA, BL
    BOKADIA, MM
    CHEMISTRY & INDUSTRY, 1966, (14) : 599 - &
  • [28] STEREOSPECIFIC SYNTHESIS OF CIS AND TRANS EPOXIDES FROM SAME DIOL
    SEELEY, DA
    MCELWEE, J
    JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (09): : 1691 - 1693
  • [29] Stereospecific synthesis of α,ω-cis- and α,ω-trans-disubstituted oxepanes
    Matsumura, R
    Suzuki, T
    Sato, K
    Inotsume, T
    Hagiwara, H
    Hoshi, T
    Kamat, VP
    Ando, M
    TETRAHEDRON LETTERS, 2000, 41 (40) : 7697 - 7700
  • [30] Interconversion of cis- and trans-Fused Oxabicyclo[5.2.0]nonan-2-ones
    Schmidt, Kerstin
    Margaretha, Paul
    HELVETICA CHIMICA ACTA, 2011, 94 (11) : 1994 - 2001