95678-51-6Relevant articles and documents
A Convenient Method for the Preparation of Methyl trans-4-Oxo-2-alkenoates
Kulinkovich, O. G.,Tischenko, I. G.,Romashin, J. N.,Savitskaya, L. N.
, p. 378 - 379 (1986)
Methyl trans-4-oxo-2-alkenoates are synthesized in 64-93percent yields by successive treatment of 5-substituted 2,2-dimethoxy-2,3-dihydrofurans with N-bromosuccinimide in aqueous acetone and triethylamine in ether.
Variation in the regioselectivity of levulinic acid bromination in ionic liquids
Zavozin, Alexander G.,Kravchenko, Natalya E.,Ignat'ev, Nikolay V.,Zlotin, Sergei G.
scheme or table, p. 545 - 547 (2010/10/02)
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.