Reaction of cycloheptatriene derivatives with 1,3-diketones in the presence of Mn(OAc)(3)

Sudemen M. B., ZENGİN M., GENÇ H., BALCI M.

TURKISH JOURNAL OF CHEMISTRY, vol.35, no.1, pp.1-11, 2011 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 35 Issue: 1
  • Publication Date: 2011
  • Doi Number: 10.3906/kim-1011-776
  • Journal Name: TURKISH JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.1-11
  • Keywords: Cycloheptatriene, norcaradiene, manganese(III) acetate, 1,3-dicarbonyl compounds, radicals, METAL-SALTS, CYCLOADDITION REACTIONS, GAMMA-LACTONES, NORCARADIENE-EQUILIBRIUM, SINGLET OXYGEN, DOUBLE-BONDS, OXIDATION, ACETATE, BENZONORBORNADIENE, PHOTOOXIDATION
  • Middle East Technical University Affiliated: Yes

Abstract

The reactions of some 1,3-dicarbonyl compounds with cycloheptatriene derivatives in the presence of Mn(OAc)(3) were examined. Cycloheptatriene forms mainly [2+3] and [6+3] dihydrofuran addition products derived from cycloheptatriene. However, the reaction of acetylacetone with cycloheptatriene substituted with an electron withdrawing group exclusively gave products derived from the norcaradiene structure. The formation mechanism of the products as well as the role of the substituent attached to cycloheptatriene is discussed.