Condensation and Michael addition reactions of aromatic aldehydes with acidic methylene compounds without catalyst

Abstract

The reactions of aromatic aldehydes with acidic methylene compounds in DMF without catalyst were studied. The condensation reaction of aromatic aldehydes (1) with 2,2-dimethyl-1,3-dioxane-4,6- dione (2) afforded 2,2-dimethyl-5-arylmethylene-1,3-dioxane-4,6- dione (3a～f). However, treatment of aromatic aldehydes (1) with 5,5-dimethyl-1,3-cyclohexanedione (4) under the same conditions afforded 2,2'-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexen-1- one) (5a～h). The crystal structure of 5b was determined by X-ray diffraction analysis.

Key words: AROMATIC ALDEHYDE, CYCLOHEXANEDIONE P, CONDENSATION REACTION, DIOXANE P, MICHAEL ADDITION REACTION, METHYLENE, DIKETONE, CRYSTAL STRUCTURE DETERMINATION

CLC Number:

O621

Cite this article

SHI DAQING;LU ZAISHENG;GAO YUAN;FENG YOUJIAN;ZHOU LONGHU;DAI GUIYUAN. Condensation and Michael addition reactions of aromatic aldehydes with acidic methylene compounds without catalyst[J]. Chin. J. Org. Chem., 1998, 18(1): 82-87.

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