Regioselective hydroxylactonization of γ,δ-unsaturated carboxylic acids with hydrogen peroxide catalyzed by methyltrioxorhenium

被引：16
|
作者：
Tan, HS
Espenson, JH [1 ]
机构：
[1] Iowa State Univ Sci & Technol, Ames Lab, Ames, IA 50011 USA
[2] Iowa State Univ Sci & Technol, Dept Chem, Ames, IA 50011 USA
来源：
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 1999年 / 142卷 / 03期
关键词：
catalysis; rhenium; peroxide; lactonization;
D O I：
10.1016/S1381-1169(98)00307-0
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The oxidation of unsaturated carboxylic acids and esters to lactones with hydrogen peroxide is catalyzed by methyltrioxorhenium (MTO). The reaction proceeds regioselectively in high yield. On the basis of the results of this investigation and a comparison with previous work, a concerted process and mechanism have been suggested. (C) 1999 Elsevier Science B.V. All rights reserved.
引用
收藏
页码：333 / 338
页数：6
相关论文
共 50 条
  • [1] Regioselective hydroxylactonization of unsaturated carboxylic acids with hydrogen peroxide catalyzed by methyltrioxorhenium.
    Tan, HS
    Espenson, JH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U1001 - U1002
  • [2] Methyltrioxorhenium catalyzed oxidative cleavage of α-hydroxycarbonyl compounds to carboxylic acids with hydrogen peroxide
    Jain, SL
    Sharma, VB
    Sain, B
    SYNTHETIC COMMUNICATIONS, 2003, 33 (22) : 3875 - 3878
  • [3] Palladium(II)-catalyzed Selective Oxidation of α,β-Unsaturated Aldehydes to α,β-Unsaturated Carboxylic Acids with Hydrogen Peroxide
    Kon, Yoshihiro
    Imao, Daisuke
    Nakashima, Takuya
    Sato, Kazuhiko
    CHEMISTRY LETTERS, 2009, 38 (05) : 430 - 431
  • [4] Selective and mild oxidation of thiols to sulfonic acids by hydrogen peroxide catalyzed by methyltrioxorhenium
    Ballistreri, Francesco P.
    Tomaselli, Gaetano A.
    Toscano, Rosa M.
    TETRAHEDRON LETTERS, 2008, 49 (20) : 3291 - 3293
  • [5] OXIDATION OF BENZALDEHYDES CATALYZED BY METHYLTRIOXORHENIUM WITH HYDROGEN-PEROXIDE
    YAMAZAKI, S
    CHEMISTRY LETTERS, 1995, (02) : 127 - 128
  • [6] Oxidation of sulfoxides by hydrogen peroxide, catalyzed by methyltrioxorhenium(VII)
    Lahti, DW
    Espenson, JH
    INORGANIC CHEMISTRY, 2000, 39 (10) : 2164 - 2167
  • [7] Oxidation of Aldehydes to Carboxylic Acids with Hydrogen Peroxide and PTSA Catalyzed by β-Cyclodextrin
    Jeong, Se Young
    Kim, Nagyeong
    Lee, Jong Chan
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2014, 35 (11) : 3366 - 3368
  • [8] Sulfonated carbon catalyzed oxidation of aldehydes to carboxylic acids by hydrogen peroxide
    Lipeng Zhou
    Beibei Dong
    Si Tang
    Hong Ma
    Chen Chen
    Jie Xu
    Xiaomei Yang
    JournalofEnergyChemistry, 2013, 22 (04) : 659 - 664
  • [9] Sulfonated carbon catalyzed oxidation of aldehydes to carboxylic acids by hydrogen peroxide
    Zhou, Lipeng
    Dong, Beibei
    Tang, Si
    Ma, Hong
    Chen, Chen
    Yang, Xiaomei
    Xu, Jie
    JOURNAL OF ENERGY CHEMISTRY, 2013, 22 (04) : 659 - 664
  • [10] Oxidation of symmetric disulfides with hydrogen peroxide catalyzed by methyltrioxorhenium(VII)
    Wang, Y
    Espenson, JH
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (01): : 104 - 107
12345