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, cilt.35, sa.1, ss.1-11, 2011 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 35 Sayı: 1
  • Basım Tarihi: 2011
  • Doi Numarası: 10.3906/kim-1011-776
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.1-11
  • Anahtar Kelimeler: 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
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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.