Reinvestigation of the sulfuric acid-catalysed cyclisation of brominated 2-alkyllevulinic acids to 3-alkyl-5-methylene-2 (5H)-furanones
AJ Manny, S Kjelleberg, N Kumar, R de Nys, RW Read…
Index: Manny, Anthony J.; Kjelleberg, Staffan; Kumar, Naresh; De Nys, Rocky; Read, Roger W.; Steinberg, Peter Tetrahedron, 1997 , vol. 53, # 46 p. 15813 - 15826
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Citation Number: 102
Abstract
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- ...
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