Stereochemistry of the intramolecular carbolithiation of vinyl sulfides

被引:18
|
作者
Hoffmann, RW [1 ]
Koberstein, R [1 ]
Remacle, B [1 ]
Krief, A [1 ]
机构
[1] FAC UNIV NOTRE DAME PAIX,DEPT CHEM,B-5000 NAMUR,BELGIUM
关键词
D O I
10.1039/a705799g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Intramolecular carbolithiation of vinyl sulfides to generate configurationally stable alpha-durylthioalkyllithium compounds at -105 degrees C in THF showed carbolithiation to be nonstereospecific regarding the newly formed lithium bearing stereocentre.
引用
收藏
页码:2189 / 2190
页数:2
相关论文
共 50 条
  • [31] THE REACTION OF VINYL SULFIDES AND ALKYL SULFIDES WITH BUTYLLITHIUM
    PARHAM, WE
    MOTTER, RF
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (09) : 2146 - 2148
  • [32] Synthesis of 1-aryl-2-vinylcycloalkanes by intramolecular carbolithiation
    Krief, A
    Remacle, B
    Mercier, J
    SYNLETT, 2000, (10) : 1443 - 1446
  • [33] Specific Features of Lanthanide Stereochemistry in Sulfides
    V. N. Serezhkin
    M. Albakajaji
    D. V. Pushkin
    L. B. Serezhkina
    Russian Journal of Inorganic Chemistry, 2020, 65 : 1879 - 1890
  • [34] Specific Features of Lanthanide Stereochemistry in Sulfides
    Serezhkin, V. N.
    Albakajaji, M.
    Pushkin, D. V.
    Serezhkina, L. B.
    RUSSIAN JOURNAL OF INORGANIC CHEMISTRY, 2020, 65 (12) : 1879 - 1890
  • [35] Tandem intermolecular-intramolecular carbolithiation: A versatile method for synthesis of cyclopentanes
    Wei, XD
    Taylor, RJK
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (02) : 409 - +
  • [36] OXIDATION OF VINYL(TRIALKYLSILYLMETHYL)SULFIDES AND ALKYL(TRIALKYLSILYLALKYL)SULFIDES
    VLASOVA, NN
    KLETSKO, FP
    NERETINA, LN
    PONOMAREVA, SM
    VORONKOV, MG
    ZHURNAL OBSHCHEI KHIMII, 1976, 46 (01): : 121 - 125
  • [37] INFRARED INTENSITIES AS A QUANTITATIVE MEASURE OF INTRAMOLECULAR INTERACTIONS .17. PHENYL AND VINYL ALKYL ETHERS AND SULFIDES
    KATRITZK.AR
    TOPSOM, RD
    PINZELLI, RF
    TETRAHEDRON, 1972, 28 (13) : 3441 - +
  • [38] Synthesis of Vinyl Sulfides and Vinylamines through Catalytic Intramolecular Hydroarylation in the Presence of FeCl3 and AgOTf
    Eom, Dahan
    Mo, Juntae
    Lee, Phil Ho
    Gao, Zhiming
    Kim, Sunggak
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (03) : 533 - 540
  • [39] Influence of the Acetylenic Substituent on the Intramolecular Carbolithiation of Alkynes: A DFT Theoretical Study
    Fressigne, Catherine
    Lhermet, Rudy
    Girard, Anne-Lise
    Durandetti, Muriel
    Maddaluno, Jacques
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19): : 9659 - 9669
  • [40] Preparation of differentially 1,3-disubstituted indolines by intramolecular carbolithiation
    Bailey, WF
    Luderer, MR
    Mealy, MJ
    TETRAHEDRON LETTERS, 2003, 44 (28) : 5303 - 5305