Elsevier

Tetrahedron Letters

Volume 53, Issue 27, 4 July 2012, Pages 3471-3473
Tetrahedron Letters

Tandem isomerization–lactonization of olefinic fatty acids using the Lewis acidic ionic liquid, choline chloride·2ZnCl2

https://doi.org/10.1016/j.tetlet.2012.04.112Get rights and content

Abstract

The tandem isomerization–lactonization of unsaturated fatty acids to their corresponding γ-lactones was carried out for the first time in the presence of a Lewis acidic ionic liquid, choline chloride·2ZnCl2. The ionic liquid initially catalyzes the stepwise migration of the double bond along the carbon chain toward the carboxyl group at the Δ4 position, which subsequently undergoes lactonization resulting in the formation of γ-lactones. This one step process allows the formation of γ-lactone in good yield with little or no formation of δ-lactones. The studied ionic liquid plays the dual role of solvent as well as catalyst.

Section snippets

Acknowledgements

Financial grant from the New Agricultural Initiative Project (NAIP), Indian Council of Agricultural Research (ICAR), Govt. of India is gratefully acknowledged.

References and notes (18)

  • Y. Zhou et al.

    Appl. Catal., A: General

    (2007)
  • N. Jain et al.

    Tetrahedron

    (2005)
  • Z. Duan et al.

    Catal. Commun.

    (2006)
  • S. Sunitha et al.

    Tetrahedron Lett.

    (2007)
  • L. Dufossé et al.

    Sci. Alim.

    (1994)
  • J.-A. Hislop et al.

    J. Agric. Food Chem.

    (2004)
  • B. Schultt et al.

    J. Agric. Food Chem.

    (2007)
  • S.C. Cermak et al.

    J. Am. Oil Chem. Soc.

    (2000)
  • M.F. Ansell et al.

    J. Chem. Soc.

    (1963)
There are more references available in the full text version of this article.

Cited by (13)

  • Highly efficient and recyclable basic ionic liquids supported on SBA-15 for the synthesis of substituted styrenes, carbinolamides, and naphthopyrans

    2017, Molecular Catalysis
    Citation Excerpt :

    However, only a few reports are available those demonstrate the systematic development of basic ILs [26–29]. In recent time efforts are being made to prepare task specific ILs by incorporating multi-functional sites in the constituent anions and cations [30–34]. Ionic liquids have demonstrated their application as replacement of organic solvents but their application as sustainable catalyst is yet to be established.

  • Ionic Liquids in the Production of Biodiesel and Other Oleochemicals

    2016, Ionic Liquids in Lipid Processing and Analysis: Opportunities and Challenges
  • Iridium-catalysed isomerising trialkylsilylation of methyl oleateq

    2013, Journal of Organometallic Chemistry
    Citation Excerpt :

    First results of hydrosilane addition to internally unsaturated fatty acid esters were published as early as 1955 by Speier, followed by a few others, but no ω-substituted products whatsoever were obtained [21]. In the last two decades, other reactions of silanes catalysed by transition metal complexes have been revealed, notably dehydrogenative silylation of terminal alkenes to produce vinylsilanes [22]. Herein, we offer an Ir(I)-catalysed dehydrogenative silylation of methyl oleate with triethylsilane leading to good yields of terminal products.

View all citing articles on Scopus
View full text