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Oxidation of 4-Alkyl-2′-Hydroxy-2-cinnamylideneacetophenones with Thallium(III) Trinitrate: A New Synthesis of (E)-3-Styrylchromones

✍ Scribed by Silva, Artur M. S. ;Cavaleiro, José A. S. ;Elguero, José

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 395 KB
Volume: 1997
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199719971009

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✦ Synopsis

Abstract

The oxidative rearrangement of (E,E)‐4‐alkyl‐2′‐hydroxy‐2‐cinnamylideneacetophenones 4, obtained by base‐catalysed aldol reaction of 2′‐hydroxyacetophenone and cinnamaldehydes with thallium(III) trinitrate, gave the corresponding 3‐alkyl‐4‐aryl‐1‐(2′‐hydroxyphenyl)‐2‐(dimethoxymethyl)‐3‐buten‐1‐ones. The cyclization of these acetal intermediates with hydrochloric acid gave (E)‐3‐styrylchromones 5. The stereochemistry of the 4‐alkyl‐2′‐hydroxy‐2‐cinnamylidene‐acetophenones 4 and 3‐styrylchromones 5 double bonds was established by NOE experiments.

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