Synthesis of 2-(2-phenylethenyl) substituted 4,5-dihydrofurans by regioselective addition of 1,3-dicarbonyl compounds to dienes promoted by cerium(IV) ammonium nitrate

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YILMAZ M., USTALAR A.

ARKIVOC, pp.202-213, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2016
  • Doi Number: 10.3998/ark.5550190.p009.455
  • Journal Name: ARKIVOC
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.202-213
  • Kocaeli University Affiliated: Yes

Abstract

Radical addition of 1,3-dicarbonyl compounds to conjugated dienes in the presence of cerium(IV) ammonium nitrate in THF produced 4,5-dihydrofurans in good to excellent yields. All radical additions occurred on the terminal double bond as regioselective. Two different dihydrofurans were obtained from the reaction of 1-phenyl-1,3-butanedione with 1-phenyl-1,3-butadiene and 3-methyl-1-phenyl-1,3-butadiene. All compounds were characterised by IR, H-1, C-13-NMR and HRMS spectra.