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
  • [41] Iridium-Catalyzed Asymmetric Hydrogenation of Unsaturated Carboxylic Acids
    Zhu, Shou-Fei
    Zhou, Qi-Lin
    ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (04) : 988 - 1001
  • [42] Iridium-catalyzed enantioselective hydrogenation of α,β-unsaturated carboxylic acids
    Li, Shen
    Zhu, Shou-Fei
    Zhang, Can-Ming
    Song, Song
    Zhou, Qi-Lin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) : 8584 - +
  • [43] Nickel-Catalyzed Decarboxylative Difluoroalkylation of ,-Unsaturated Carboxylic Acids
    Li, Gang
    Wang, Tao
    Fei, Fan
    Su, Yi-Ming
    Li, Yan
    Lan, Quan
    Wang, Xi-Sheng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (10) : 3491 - 3495
  • [44] Organophotoredox/Copper Hybrid Catalysis for Regioselective Allylic Aminodecarboxylation of β,γ-Unsaturated Carboxylic Acids
    Manick, Anne-Doriane
    Tanaka, Hirotaka
    Oisaki, Kounosuke
    Kanai, Motomu
    SYNTHESIS-STUTTGART, 2018, 50 (15): : 2936 - 2947
  • [45] Substrate-directed regioselective alkene functionalizations of (E)-β,γ-unsaturated carboxylic acids
    Chang, Chi-Hao
    Yen, Chao-Ting
    Goncalves, Theo P.
    Lin, Yu-Sheng
    Wang, Yu-Chun
    Basha, R. Sidick
    Chen, Bo-Yan
    Fu, Cheng-Hao
    Chen, Liang-Wei
    Jhou, Meng-Li
    Huang, Kuo-Wei
    Chou, Chih-Ming
    CHEMICAL COMMUNICATIONS, 2024, 60 (80) : 11339 - 11342
  • [46] Transition-Metal-Catalyzed Regioselective Arylation and Vinylation of Carboxylic Acids
    Satoh, Tetsuya
    Miura, Masahiro
    SYNTHESIS-STUTTGART, 2010, (20): : 3395 - 3409
  • [47] Highly regioselective intramolecular hydroxymethylation of alpha,beta-unsaturated carboxylic acids
    Linker, T
    Maurer, M
    Rebien, F
    TETRAHEDRON LETTERS, 1996, 37 (46) : 8363 - 8366
  • [48] Palladium-catalyzed regioselective decarboxylative hydroarylation of alkynyl carboxylic acids with arylboronic acids
    Dong, Zheng
    Tong, Ren-Jie
    Xu, Lei
    Xu, Hua-Jian
    Xu, Jun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (20) : 4220 - 4224
  • [49] Oxidative cleavage of N,N-dimethylhydrazones to ketones with hydrogen peroxide, catalyzed by methyltrioxorhenium(VII)
    Stankovic, S
    Espenson, JH
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07): : 2218 - 2221
  • [50] REACTION OF ALPHA,BETA-UNSATURATED ALDEHYDES WITH HYDROGEN-PEROXIDE CATALYZED BY BENZENESELENINIC ACIDS AND THEIR PRECURSORS
    SYPER, L
    TETRAHEDRON, 1987, 43 (12) : 2853 - 2871
12345