Tribromoisocyanuric acid: A new reagent for regioselective cobromination of alkenes

被引：85
|
作者：
de Almeida, Leonardo S. [1 ]
Esteves, Pierre M. [1 ]
de Mattos, Marcio C. S. [1 ]
机构：
[1] Univ Fed Rio de Janeiro, Dept Quim Organ, Inst Quim, BR-21945970 Rio De Janeiro, Brazil
来源：
SYNLETT | 2006年 / 10期
关键词：
alkenes; cohalogenation; Oxonel (R); tribromoisocyanuric acid;
D O I：
10.1055/s-2006-941601
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple one-step method for the preparation of tribromoisocyanuric acid in good yield (87%) has been developed. The reaction of tribromoisocyanuric acid with alkenes in presence of nucleophilic solvents (MeOH, i-PrOH, AcOH and a mixture of H2O-acetone, 1:5) led to the corresponding beta-bromoethers, beta-bromoacetates and bromohydrins, in high regioselectivity and good yields (73-98%).
引用
收藏
页码：1515 / 1518
页数：4
相关论文
共 50 条
  • [1] Tribromoisocyanuric Acid: A Green and Versatile Reagent
    de Almeida, Leonardo S.
    Esteves, Pierre M.
    de Mattos, Marcio C. S.
    CURRENT GREEN CHEMISTRY, 2014, 1 (02) : 94 - 107
  • [2] Dichloroiodoisocyanuric Acid: A New Reagent for Regioselective Coiodination of Alkenes and Iodination of Activated Arenes
    da Silva Ribeiro, Rodrigo
    Esteves, Pierre M.
    de Mattos, Marcio C. S.
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2012, 23 (02) : 228 - 235
  • [3] Triiodoisocyanuric acid: a new and convenient reagent for regioselective coiodination of alkenes and enolethers with oxygenated nucleophiles
    Ribeiro, Rodrigo da S.
    Esteves, Pierre M.
    de Mattos, Marcio C. S.
    TETRAHEDRON LETTERS, 2007, 48 (49) : 8747 - 8751
  • [4] Tribromoisocyanuric acid as a green reagent for benzylic bromination of alkylarenes
    de Almeida, Leonardo S.
    Esteves, Pierre M.
    de Mattos, Marcio C. S.
    TETRAHEDRON LETTERS, 2015, 56 (49) : 6843 - 6845
  • [5] Tribromoisocyanuric acid/NaNO2:: a new reagent for mononitration of phenols under mild and heterogeneous conditions
    Niknam, Khodabakhsh
    Zolfigol, Mohammad Ali
    Madrakian, Elaheh
    Ghaemi, Ezat
    SOUTH AFRICAN JOURNAL OF CHEMISTRY-SUID-AFRIKAANSE TYDSKRIF VIR CHEMIE, 2007, 60 : 109 - 112
  • [6] Triiodoisocyanuric acid: a new and convenient reagent for regioselective iodination of activated arenes
    Ribeiro, Rodrigo da S.
    Esteves, Pierre M.
    de Mattos, Marcio C. S.
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2008, 19 (07) : 1239 - 1243
  • [7] Efficient electrophilic cobromination of alkenes and bromination of activated arenes with bromodichloroisocyanuric acid under mild conditions
    de Almeida, Leonardo S.
    Esteves, Pierre M.
    de Mattos, Marcio C. S.
    SYNLETT, 2007, (11) : 1687 - 1690
  • [8] N-Iodosuccinimide: A Highly Effective Regioselective Reagent for Iodoesterification of Alkenes
    Reddy, Aleti R.
    Sangwan, Payare L.
    Chinthakindi, Praveen K.
    Farooq, Saleem
    Siddaiah, Vidavalur
    Koul, Surrinder
    HELVETICA CHIMICA ACTA, 2013, 96 (07) : 1313 - 1324
  • [9] Tribromoisocyanuric Acid as a Green Cohalogenating Reagent: An Efficient Transformation of Alkynes into α,α-Dibromoketones and Vicinal Dibromoalkenes
    Crespo, Livia T. C.
    Senra, Monica R.
    Esteves, Pierre M.
    de Mattos, Marcio C. S.
    LETTERS IN ORGANIC CHEMISTRY, 2019, 16 (08) : 627 - 632
  • [10] Tribromoisocyanuric Acid (TBCA)
    Hoelz, Lucas V. B.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2010, 63 (08) : 1307 - 1307
12345