Catalytic oxidation of catechins to p-benzoquinones with hydrogen peroxide/methyltrioxorhenium

被引：19
作者：
Bernini, R
Mincione, E
Provenzano, G
Fabrizi, G
机构：
[1] Univ Tuscia, Dipartimento ABAC, I-01100 Viterbo, Italy
[2] Consorzio Interuniv Chim Ambiente, Unita Ric VT2, I-30175 Marghera, VE, Italy
[3] Univ Roma La Sapienza, Dipartimento Chim & Tecnol Sostanze Biologicament, I-00185 Rome, Italy
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 17期
关键词：
hydrogen peroxide/methyltrioxorhenium; catalytic oxidations; catechins; p-benzoquinones; winery by-products; renewable sources; agroindustrial wastes;
D O I：
10.1016/j.tetlet.2005.03.032
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New p-benzoquinones were obtained by oxidation of catechin and epicatechin derivatives with the hydrogen peroxide/methyltrioxorhenium catalytic system. Reactions were carried out both in homogeneous and heterogeneous conditions and proceeded with high conversion and moderate yields. Polymer-supported methyltrioxorhenium systems were used as heterogeneous catalysts. After the first oxidation, the catalytic systems can be recovered and reused for five consecutive times without loss of stability and efficiency. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2993 / 2996
页数：4
相关论文
共 40 条
  • [1] OXIDATION OF METHOXYBENZENES TO P-BENZOQUINONES CATALYZED BY METHYLTRIOXORHENIUM(VII)
    ADAM, W
    HERRMANN, WA
    SAHAMOLLER, CR
    SHIMIZU, M
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 97 (01) : 15 - 20
  • [2] CATALYTIC-OXIDATION OF PHENOLS TO P-QUINONES WITH THE HYDROGEN-PEROXIDE AND METHYLTRIOXORHENIUM(VII) SYSTEM
    ADAM, W
    HERRMANN, WA
    LIN, JH
    SAHAMOLLER, CR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) : 8281 - 8283
  • [3] ADAM W, 1994, SYNTHESIS-STUTTGART, P560
  • [4] AGRAWAL PK, 1989, CARBON 13 NMR FLAVON, P434
  • [5] OXIDATION OF CATECHOL AND OF 2,6-DI-TERT-BUTYLPHENOL BY DIOXIRANES
    ALTAMURA, A
    FUSCO, C
    D'ACCOLTI, L
    MELLO, R
    PRENCIPE, T
    CURCI, R
    [J]. TETRAHEDRON LETTERS, 1991, 32 (40) : 5445 - 5448
  • [6] Catechin contents of foods commonly consumed in The Netherlands. 1. Fruits, vegetables, staple foods, and processed foods
    Arts, ICW
    van de Putte, B
    Hollman, PCH
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (05) : 1746 - 1751
  • [7] Free radicals and grape seed proanthocyanidin extract: importance in human health and disease prevention
    Bagchi, D
    Bagchi, M
    Stohs, SJ
    Das, DK
    Ray, SD
    Kuszynski, CA
    Joshi, SS
    Pruess, HG
    [J]. TOXICOLOGY, 2000, 148 (2-3) : 187 - 197
  • [8] CH3ReO3/H2O2 in room temperature ionic liquids:: an homogeneous recyclable catalytic system for the Baeyer-Villiger reaction
    Bernini, R
    Coratti, A
    Fabrizi, G
    Goggiamani, A
    [J]. TETRAHEDRON LETTERS, 2003, 44 (50) : 8991 - 8994
  • [9] Conversion of naringenin and hesperetin by heterogeneous catalytic Baeyer-Villiger reaction into lactones exhibiting apoptotic activity
    Bernini, R
    Mincione, E
    Cortese, M
    Saladino, R
    Gualandi, G
    Belfiore, MC
    [J]. TETRAHEDRON LETTERS, 2003, 44 (26) : 4823 - 4825
  • [10] A new and efficient Baeyer-Villiger rearrangement of flavanone derivatives by the methyltrioxorhenium/H2O2 catalytic system
    Bernini, R
    Mincione, E
    Cortese, M
    Aliotta, G
    Oliva, A
    Saladino, R
    [J]. TETRAHEDRON LETTERS, 2001, 42 (32) : 5401 - 5404
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