Elucidation of the reaction mechanism for the palladium-catalyzed synthesis of vinyl acetate

被引:59
|
作者
Stacchiola, D
Calaza, F
Burkholder, L
Schwabacher, AW
Neurock, M
Tysoe, WT [1 ]
机构
[1] Univ Wisconsin, Dept Chem & Biochem, Milwaukee, WI 53211 USA
[2] Univ Wisconsin, Surface Studies Lab, Milwaukee, WI 53211 USA
[3] Univ Virginia, Dept Chem Engn, Charlottesville, VA 22904 USA
关键词
IR spectroscopy; isotopes; palladium; reaction mechanisms; surface chemistry;
D O I
10.1002/anie.200500782
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Finding the right pathway: Reaction of isotopomers of ethylene with acetate species (see scheme) adsorbed on a Pd(111) surface in ultrahigh vacuum has shown that vinyl acetate is produced by insertion of ethylene into the acetate species to form an acetoxyethyl intermediate, which decomposes by β-hydride elimination to yield vinyl acetate. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4572 / 4574
页数:3
相关论文
共 50 条
  • [21] Synthesis of Cyclooctatetraenes through a Palladium-Catalyzed Cascade Reaction
    Blouin, Sarah
    Gandon, Vincent
    Blond, Gaelle
    Suffert, Jean
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (25) : 7208 - 7211
  • [22] Stereoselectivity of stilbene synthesis by palladium-catalyzed Heck reaction
    Clark, Kyle
    Werner, Nathan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [23] Theoretical Study on the Mechanism of Palladium-Catalyzed Dearomatization Reaction of Chloromethylnaphthalene
    Ren, Ying
    Jia, Jianfeng
    Liu, Wenxian
    Wu, Hai-Shun
    ORGANOMETALLICS, 2013, 32 (01) : 52 - 62
  • [24] Palladium-catalyzed Suzuki-Miyaura reaction of fluorinated vinyl chloride: a new approach for synthesis α and α,β-trifluoromethylstyrenes
    Li, Yang
    Zhao, Bo
    Dai, Kun
    Tu, Dong-Huai
    Wang, Bo
    Wang, Yao-Yu
    Liu, Zhao-Tie
    Liu, Zhong-Wen
    Lu, Jian
    TETRAHEDRON, 2016, 72 (37) : 5684 - 5690
  • [25] Synthesis of Vinyl Triazenes by Palladium-Catalyzed Addition Reactions to Alkynyl Triazenes
    Suleymanov, Abdusalom A.
    Scopelliti, Rosario
    Tirani, Farzaneh Fadaei
    Severin, Kay
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (21) : 4178 - 4183
  • [26] AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL AND ARYL HALIDES OR TRIFLATES WITH TERMINAL ALKYNES
    ALAMI, M
    FERRI, F
    LINSTRUMELLE, G
    TETRAHEDRON LETTERS, 1993, 34 (40) : 6403 - 6406
  • [27] Palladium-catalyzed reaction of functionalized β-trifluoromethyl vinyl bromides with terminal alkynes and alkenes
    Legros, J
    Crousse, B
    Bonnet-Delpon, D
    Bégué, JP
    JOURNAL OF FLUORINE CHEMISTRY, 2001, 107 (01) : 121 - 125
  • [28] Palladium-Catalyzed Dimerization of Vinyl Ethers: Mechanism, Catalyst Optimization, and Polymerization Applications
    Hong, Changwen
    Wang, Xingbao
    Chen, Changle
    MACROMOLECULES, 2019, 52 (18) : 7123 - 7129
  • [29] AN UNUSUAL MECHANISM OF A PALLADIUM-CATALYZED INTRAMOLECULAR CARBAMETALATION - A NOVEL PALLADIUM-CATALYZED REARRANGEMENT
    TROST, BM
    TANOURY, GJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) : 1636 - 1638
  • [30] PALLADIUM-CATALYZED COUPLING OF VINYL EPOXIDES WITH ORGANOSTANNANES
    ECHAVARREN, AM
    TUETING, DR
    STILLE, JK
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) : 4039 - 4041