Catalytic oxidative cleavage of olefins promoted by osmium tetroxide and hydrogen peroxide

被引:46
作者
Hart, Stewart R. [1 ]
Whitehead, Daniel C. [1 ]
Travis, Benjamin R. [1 ]
Borhan, Babak [1 ]
机构
[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
关键词
ADIPIC ACID; OZONOLYSIS; LACTONIZATION; OZONE; OXONE; BONDS; WATER;
D O I
10.1039/c0ob01189d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hydrogen peroxide was employed as the terminal oxidant in the osmium tetroxide mediated oxidative cleavage of olefins, producing the corresponding aldehyde and ketone products. Aryl olefins are cleaved in good to excellent yield regardless of arene electronics. Alkyl olefins cleave in moderate to good yield for di- and tri-substituted alkenes.
引用
收藏
页码:4741 / 4744
页数:4
相关论文
共 21 条
  • [1] THE REACTIONS OF OZONE WITH ORGANIC COMPOUNDS
    BAILEY, PS
    [J]. CHEMICAL REVIEWS, 1958, 58 (05) : 925 - 1010
  • [2] MECHANISM OF OZONOLYSIS
    CRIEGEE, R
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (11): : 745 - 752
  • [3] Oxidative Cleavage with Hydrogen Peroxide: Preparation of Polycarboxylic Acids from Cyclic Olefins
    Fujitani, Kango
    Mizutani, Toshihiro
    Oida, Tatsuo
    Kawase, Tokuzo
    [J]. JOURNAL OF OLEO SCIENCE, 2009, 58 (01) : 37 - 42
  • [4] Polymer Supported Vanadium Complexes as Catalysts for the Oxidation of Alkenes in Water
    Hsiao, Ming-Chieh
    Liu, Shiuh-Tzung
    [J]. CATALYSIS LETTERS, 2010, 139 (1-2) : 61 - 66
  • [5] Explosion hazard of gaseous ozone
    Koike, K
    Inoue, G
    Fukuda, T
    [J]. JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, 1999, 32 (03) : 295 - 299
  • [6] Larock R.C., 1999, COMPREHENSIVE ORGANI, V2nd, P1213
  • [7] Mechanistic insights into the conversion of cyclohexene to adipic acid by H2O2 in the presence of a TAPO-5 catalyst
    Lee, SO
    Raja, R
    Harris, KDM
    Thomas, JM
    Johnson, BFG
    Sankar, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (13) : 1520 - 1523
  • [8] Green oxidation with aqueous hydrogen peroxide
    Noyori, R
    Aoki, M
    Sato, K
    [J]. CHEMICAL COMMUNICATIONS, 2003, (16) : 1977 - 1986
  • [9] OSMIUM TETROXIDE-CATALYZED PERIODATE OXIDATION OF OLEFINIC BONDS
    PAPPO, R
    ALLEN, DS
    LEMIEUX, RU
    JOHNSON, WS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (04) : 478 - 479
  • [10] Indium(III) chloride-catalyzed oxidative cleavage of carbon-carbon multiple bonds by tert-butyl hydroperoxide in water -: a safer alternative to ozonolysis
    Ranu, Brindaban C.
    Bhadra, Sukalyan
    Adak, Laksmikanta
    [J]. TETRAHEDRON LETTERS, 2008, 49 (16) : 2588 - 2591