140663-07-6Relevant academic research and scientific papers
Variation in the regioselectivity of levulinic acid bromination in ionic liquids
Zavozin, Alexander G.,Kravchenko, Natalya E.,Ignat'ev, Nikolay V.,Zlotin, Sergei G.
, p. 545 - 547 (2010)
The reaction of levulinic acid and its esters with bromine in ionic liquids results in the formation of 3-bromo derivatives as the major products and not the 5-bromo substituted isomers, which are typically formed in organic solvents. The bromination of l
Reinvestigation of the sulfuric acid-catalysed cyclisation of brominated 2-alkyllevulinic acids to 3-alkyl-5-methylene-2(5H)-furanones
Manny, Anthony J.,Kjelleberg, Staffan,Kumar, Naresh,De Nys, Rocky,Read, Roger W.,Steinberg, Peter
, p. 15813 - 15826 (2007/10/03)
A synthesis of ethyl-, butyl-, hexyl- and dodecyl-substituted fimbrolides from alkyl-substituted levulinic acid derivatives through bromination and acid promoted lactonisation is described. The underlying reactions have been investigated using levulinic acid as a model, and the effects of varying the bromination conditions and changing acid concentration on product distribution are discussed. Dibromination proceeds best in CHCl3 and proceeds in EtOH-free CHCl3 without the complication of ester formation. Cyclisation. occurs with concomitant oxidation in 98-100% H2SO4 but gives highest yields of fimbrolides in 100% H2SO4. The formation of related beckerelide substances is also described.
