Cross-metathesis transformations of terpenoids in dialkyl carbonate solvents

被引：65
作者：
Bilel, Hallouma [1 ,2 ]
Hamdi, Naceur [1 ]
Zagrouba, Fethy [1 ]
Fischmeister, Cedric [2 ]
Bruneau, Christian [2 ]
机构：
[1] Univ 7 November Carthage, Higher Inst Sci & Technol Environm Borj Cedria, Hammam Lif 2050, Tunisia
[2] Univ Rennes 1, CNRS, UMR 6226, F-35042 Rennes, France
来源：
GREEN CHEMISTRY | 2011年 / 13卷 / 06期
关键词：
RING-CLOSING METATHESIS; FATTY-ACID ESTERS; ENVIRONMENTALLY FRIENDLY SOLVENT; OLEFIN-METATHESIS; DIMETHYL CARBONATE; ORGANIC CARBONATES; CATALYTIC METATHESIS; ALTERNATIVE SOLVENTS; PROPYLENE CARBONATE; RENEWABLE MATERIALS;
D O I：
10.1039/c1gc15024c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The ruthenium catalysed cross-metathesis of terpenoids with methyl acrylate and methyl methacrylate was used to prepare new terpenoids and to improve, to a large extent, the synthesis of known terpenoids. In particular, the cross-metathesis of mono-unsaturated terpenoids was very efficient whereas the transformation of terpenoids incorporating two double bonds was more difficult due to side reactions. The cross-metathesis reactions were carried out under environmentally friendly conditions either in dimethyl carbonate or under solvent-free conditions.
引用
收藏
页码：1448 / 1452
页数：5
相关论文
共 77 条
  • [1] Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation
    Alfonsi, Kim
    Colberg, Juan
    Dunn, Peter J.
    Fevig, Thomas
    Jennings, Sandra
    Johnson, Timothy A.
    Kleine, H. Peter
    Knight, Craig
    Nagy, Mark A.
    Perry, David A.
    Stefaniak, Mark
    [J]. GREEN CHEMISTRY, 2008, 10 (01) : 31 - 36
  • [2] [Anonymous], [No title captured]
  • [3] Diethyl carbonate as a solvent for ruthenium catalysed C-H bond functionalisation
    Arockiam, Percia
    Poirier, Valentin
    Fischmeister, Cedric
    Bruneau, Christian
    Dixneuf, Pierre H.
    [J]. GREEN CHEMISTRY, 2009, 11 (11) : 1871 - 1875
  • [4] Propylene carbonate as a solvent for asymmetric Hydrogenations
    Bayardon, Jerome
    Holz, Jens
    Schaeffner, Benjamin
    Andrushko, Vasyl
    Verevkin, Sergej
    Preetz, Angelika
    Boerner, Armin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (31) : 5971 - 5974
  • [5] Behr A, 2002, ADV SYNTH CATAL, V344, P1142, DOI 10.1002/1615-4169(200212)344:10<1142::AID-ADSC1142>3.0.CO
  • [6] 2-P
  • [7] Myrcene as a Natural Base Chemical in Sustainable Chemistry: A Critical Review
    Behr, Arno
    Johnen, Leif
    [J]. CHEMSUSCHEM, 2009, 2 (12) : 1072 - 1095
  • [8] Dimethyl carbonate:: an environmentally friendly solvent for hydrogen peroxide (H2O2)/methyltrioxorhenium (CH3ReO3, MTO) catalytic oxidations
    Bernini, Roberta
    Mincione, Enrico
    Barontini, Maurizio
    Crisante, Fernanda
    Fabrizi, Giancarlo
    Gambacorta, Augusto
    [J]. TETRAHEDRON, 2007, 63 (29) : 6895 - 6900
  • [9] In situ tandem allylic acetate isomerisation-ring closing metathesis: 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ruthenium benzylidenes and palladium(0)-phosphine combinations
    Braddock, DC
    Matsuno, A
    [J]. TETRAHEDRON LETTERS, 2002, 43 (18) : 3305 - 3308
  • [10] Breitmaier E., 2006, TERPENES, DOI 10.1002/9783527609949
12345678