Unusual phase transfer mechanism of the ruthenium-catalyzed oxidation of alcohols with hydrogen peroxide

被引:21
|
作者
Rothenberg, G [1 ]
Barak, G [1 ]
Sasson, Y [1 ]
机构
[1] Hebrew Univ Jerusalem, Casali Inst Appl Chem, IL-91904 Jerusalem, Israel
关键词
D O I
10.1016/S0040-4020(99)00206-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A kinetic investigation of the Ru-catalyzed oxidation of I-phenyl ethanol to acetophenone using KO, under PT conditions shows that this system differs from classic extraction and interfacial mechanisms often encountered in PTC oxidations. Vesicles formed by the phase transfer agent in the organic phase are proposed as the catalytic reaction sites. Such structures are evidenced by microscopic studies. The effects of substituents, different phase transfer agents, and metal catalysts are studied and discussed in view of this mechanism. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6301 / 6310
页数:10
相关论文
共 50 条
  • [41] Ruthenium-catalyzed β-alkylation of secondary alcohols with primary alcohols
    Bai, Wei
    Jia, Guochen
    INORGANICA CHIMICA ACTA, 2015, 431 : 234 - 241
  • [42] Ruthenium-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols
    Cheung, Hung Wai
    Lee, Ting Yan
    Lui, Ho Yin
    Yeung, Chi Hung
    Lau, Chak Po
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (18) : 2975 - 2983
  • [43] ON THE MECHANISM OF THE RUTHENIUM-CATALYZED RECONSTITUTIVE CONDENSATION OF ALLYLIC ALCOHOLS AND TERMINAL ALKYNES
    TROST, BM
    KULAWIEC, RJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) : 5579 - 5584
  • [44] Microwave-mediated ruthenium-catalyzed asymmetric hydrogen transfer
    Lutsenko, S
    Moberg, C
    TETRAHEDRON-ASYMMETRY, 2001, 12 (18) : 2529 - 2532
  • [45] Exploring Tandem Ruthenium-Catalyzed Hydrogen Transfer and SNAr Chemistry
    Polidano, Kurt
    Reed-Berendt, Benjamin G.
    Basset, Anais
    Watson, Andrew J. A.
    Williams, Jonathan M. J.
    Morrill, Louis C.
    ORGANIC LETTERS, 2017, 19 (24) : 6716 - 6719
  • [46] Ruthenium-Catalyzed Synthesis of Quinazolinones through Hydrogen Transfer and Cyclization
    Qiao, Jingyi
    Jiang, Hongshuo
    Liu, Xiaochong
    Xu, Chunzhao
    Sun, Zhizhong
    Chu, Wenyi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (13) : 2428 - 2434
  • [47] KINETICS AND MECHANISM OF ALDEHYDE OXIDATION BY HYDROGEN-PEROXIDE IN ALCOHOLS CATALYZED BY SELEN DIOXIDE
    PIKH, ZG
    MARSHALOK, GA
    YATCHISHIN, II
    UKRAINSKII KHIMICHESKII ZHURNAL, 1982, 48 (05): : 529 - 531
  • [48] RUTHENIUM-CATALYZED OXIDATION OF ALCOHOLS AND CATECHOLS USING TERT-BUTYL HYDROPEROXIDE
    TSUJI, Y
    OHTA, T
    IDO, T
    MINBU, H
    WATANABE, Y
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1984, 270 (03) : 333 - 341
  • [49] CONTROLLING FACTORS IN THE RUTHENIUM-CATALYZED OXIDATION OF PRIMARY ALCOHOLS WITH SODIUM-BROMATE
    BEHR, A
    EUSTERWIEMANN, K
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 403 (1-2) : 209 - 214
  • [50] Frontispiece: Simple and Efficient Ruthenium-Catalyzed Oxidation of Primary Alcohols with Molecular Oxygen
    Ray R.
    Chandra S.
    Maiti D.
    Lahiri G.K.
    Ray, Ritwika (ritwika@chem.iitb.ac.in), 1600, Wiley-VCH Verlag (22):