One-step preparation of symmetrical 1,4-diketones from alpha-halo ketones in the presence of Zn-I-2 as a condensation agent

CEYLAN M., GURDERE M. B., BUDAK Y., Kazaz C., Secen H.

SYNTHESIS-STUTTGART, sa.11, ss.1750-1754, 2004 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2004
  • Doi Numarası: 10.1055/s-2004-829118
  • Dergi Adı: SYNTHESIS-STUTTGART
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1750-1754
  • Anahtar Kelimeler: 1,4-diketones, alpha-bromoketones, zinc, ACTIVATED DOUBLE-BONDS, ALDEHYDES, DIKETONES, ESTER
  • Atatürk Üniversitesi Adresli: Evet

Özet

Eleven 1,4-diphenylbutane-1,4-diones have been prepared in one step from the corresponding a-halo acetophenones under the action of Zn-I-2 as a condensation agent with moderate to high yields. The mechanistic pathway of the reaction can be explained by the Wurtz-like self-condensation of a-halo ketones. Similarly, 3-chloropentane-2,4-dione gave 3,4-diacetylhexane-2,5-dione, a Wurtz-like condensation product.