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 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 35 Issue: 1
  • Publication Date: 2011
  • Doi Number: 10.3906/kim-1011-776
  • Title of Journal : TURKISH JOURNAL OF CHEMISTRY
  • 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

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.