One-Step Preparation of Symmetrical 1,4-Diketones from α-Halo Ketones in the Presence of Zn-I2 as a Condensation Agent

Mustafa Ceylan; M. Burcu Gürdere; Yakup Budak; Cavit Kazaz; Hasan Seçen

doi:10.1055/s-2004-829118

PAPER

One-Step Preparation of Symmetrical 1,4-Diketones from α-Halo Ketones in the Presence of Zn-I₂ as a Condensation Agent

Mustafa Ceylan*^a, M. Burcu Gürdere^a, Yakup Budak^a, Cavit Kazaz^b, Hasan Seçen^b
^a Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, 60250 Tokat, Turkey
Fax: +90(356)2521585; e-Mail: mceylan@gop.edu.tr;
^b Department of Chemistry, Faculty of Arts and Sciences, Atatürk University, 25250 Erzurum, Turkey

Abstract

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Abstract

Eleven 1,4-diphenylbutane-1,4-diones have been prepared in one step from the corresponding α-halo acetophenones under the action of Zn-I₂ 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 α-halo ketones. Similarly, 3-chloropentane-2,4-dione gave 3,4-diacetylhexane-2,5-dione, a Wurtz-like condensation product.

Key words

1,4-Diketones - α-bromoketones - zinc

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