Reactions of acylpolysilanes with silyl Lewis acids

被引：8
|
作者：
Berry, MB
Griffiths, RJ
Howard, JAK
Leech, MA
Steel, PG
Yufit, DS
机构：
[1] Univ Durham, Dept Chem, Sci Labs, Durham DH1 3LE, England
[2] Glaxo Wellcome Res & Dev Ltd, Stevenage SG1 2NY, Herts, England
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 24期
关键词：
D O I：
10.1039/a906377c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of acylpolysilanes with TMSOT and TMS(NTf2) proceed via a series of 1,2 silyl and silyoxy shifts to afford the silanol products 5 and 6 respectively. A unified mechanistic pathway involving the formation of transient silenium ion complexes and silenes which rationalises these products is proposed. The structural assignment of the products is supported by X-ray structures for the phenyl 6a and trifluoromethylphenyl 6b substituted silanols.
引用
收藏
页码：3645 / 3650
页数：6
相关论文
共 50 条
  • [31] Asymmetric aldol addition of aldehydes to a difluoroketene silyl acetal catalyzed by chiral Lewis acids
    Iseki, K
    Kuroki, Y
    Asada, D
    Takahashi, M
    Kishimoto, S
    Kobayashi, Y
    TETRAHEDRON, 1997, 53 (30) : 10271 - 10280
  • [32] Asymmetric Aldol Addition of Aldehydes to a Difluoroketene Silyl Acetal Catalyzed by Chiral Lewis Acids
    Tetrahedron, 30 (10271):
  • [33] Lewis base activation of Lewis acids: Catalytic, enantioselective addition of glycolate-derived silyl ketene acetals to aldehydes
    Denmark, Scott E.
    Chung, Won-jin
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12): : 4582 - 4595
  • [34] REACTIONS OF TRIHALODITHIATRIAZINES AND TRIFLUOROTRIAZINE WITH HALOGEN-LEWIS-ACIDS
    CHEN, SJ
    BEHRENS, U
    OLBRICH, F
    MEWS, R
    ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1993, 619 (10): : 1725 - 1728
  • [35] CHIRAL LEWIS-ACIDS IN CATALYTIC ASYMMETRIC REACTIONS
    NARASAKA, K
    SYNTHESIS-STUTTGART, 1991, (01): : 1 - 11
  • [36] Applications of Selenonium Cations as Lewis Acids in Organocatalytic Reactions
    He, Xinxin
    Wang, Xinyan
    Tse, Ying-Lung
    Ke, Zhihai
    Yeung, Ying-Yeung
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (39) : 12869 - 12873
  • [37] REACTIONS OF CYCLO-THIAZYLHALIDES WITH LEWIS-ACIDS
    MEWS, R
    WAGNER, DL
    GLEMSER, O
    ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1975, 412 (02): : 148 - 154
  • [38] A MECHANISTIC TEST FOR REACTIONS CATALYZED BY LEWIS-ACIDS
    LASZLO, P
    TESTONHENRY, M
    TETRAHEDRON LETTERS, 1991, 32 (31) : 3837 - 3838
  • [39] Lewis acids as co-reagents in sulfenylation reactions
    N. V. Zyk
    A. Yu. Gavrilova
    O. A. Mukhina
    O. B. Bondarenko
    N. S. Zefirov
    Russian Journal of Organic Chemistry, 2011, 47 : 608 - 610
  • [40] How Lewis Acids Catalyze Diels–Alder Reactions
    Vermeeren, Pascal
    Hamlin, Trevor A.
    Fernández, Israel
    Bickelhaupt, F. Matthias
    Bickelhaupt, F. Matthias (f.m.bickelhaupt@vu.nl); Fernández, Israel (israel@quim.ucm.es), 1600, John Wiley and Sons Inc (132): : 6260 - 6265
12345