Oxidation of 4-Alkyl-2′-Hydroxy-2-cinnamylideneacetophenones with Thallium(III) Trinitrate: A New Synthesis of (E)-3-Styrylchromones
作者： Artur M. S. Silva , José A. S. Cavaleiro , José Elguero
DOI: 10.1002/JLAC.199719971009
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摘要: The oxidative rearrangement of (E,E)-4-alkyl-2′-hydroxy-2-cinnamylideneacetophenones 4, obtained by base-catalysed aldol reaction 2′-hydroxyacetophenone and cinnamaldehydes with thallium(III) trinitrate, gave the corresponding 3-alkyl-4-aryl-1-(2′-hydroxyphenyl)-2-(dimethoxymethyl)-3-buten-1-ones. cyclization these acetal intermediates hydrochloric acid (E)-3-styrylchromones 5. stereochemistry 4-alkyl-2′-hydroxy-2-cinnamylidene-acetophenones 4 3-styrylchromones 5 double bonds was established NOE experiments.
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