One Step Preparation of 1,4-Diketones from Methyl Ketones and α-Bromomethyl Ketones in the Presence of ZnCl2 · t-BuOH · Et2NR as a Condensation Agent

Natali M. Nevar; Alexander V. Kel'in; Oleg G. Kulinkovich

doi:10.1055/s-2000-6418

Synthesis 2000; 2000(9): 1259-1262
DOI: 10.1055/s-2000-6418

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One Step Preparation of 1,4-Diketones from Methyl Ketones and α-Bromomethyl Ketones in the Presence of ZnCl₂ · t-BuOH · Et₂NR as a Condensation Agent

Natali M. Nevar^* , Alexander V. Kel'in †, Oleg G. Kulinkovich

^*Department of Chemistry, Belarussian State University, Fr. Skorina Av. 4, 220080 Minsk, Belarus; Fax (1 72)20 88 21; E-mail: organic@chem.bsu.unibel.by

Abstract

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1,4-Diketones have been prepared in one step from methyl ketones and α-bromomethyl ketones under the action of ZnCl₂ · t-BuOH · Et₂NR as a condensation agent with moderate to high yields. The mechanistic pathway of the reaction is proposed to go through aldol condensation of ketones followed by 1,3-dehydrobromination of aldol products and cleavage of activated cyclopropyl intermediates.

α-bromo ketones - 1,4-diketones - aldol condensation - 3-bromo-2-hydroxy ketones - activated cyclopropanes

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