Solvent effect on the reversibility of base catalyzed Henry reactions : Triton B catalyzed nitro aldol reactions in alcohol

F. Ono, Hiroe Soejima, J. Tanaka, S. Kanemasa
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Abstract

The amine catalyzed nitro aldol reactions between nitromethane and aldehydes are found to be reversible in an alcohol solvent on the basis of the reaction monitoring by 1H NMR spectroscopy. The reaction in alcohols is particularly rapid to complete the equilibrium in a short period of time at room temperature, producing nitro aldol product in high yields. Triton B is especially effective as catalyst in the nitro aldol reactions of nitromethane in methanol. Only a small catalytic loading of triton B as small as 1 mol% is enough to finish the reaction. Aromatic, aliphatic, and {alpha},{beta}-unsaturated aldehydes as well as aldehyde hydrates and aqueous aldehydes are successfully employed.
溶剂对碱催化Henry反应可逆性的影响:Triton B在醇中催化硝基醇反应
通过1H NMR监测,发现胺催化硝基甲烷与醛之间的硝基醛反应在醇溶剂中可逆。该反应在醇类中的反应速度特别快,在室温下可在短时间内完成平衡,产率高。在硝基甲烷在甲醇中的硝基醇反应中,Triton B是特别有效的催化剂。只需要少量的triton B催化负荷(1mol %)就足以完成反应。芳香族,脂肪族,和{α},{β}-不饱和醛以及醛水合物和水醛被成功地使用。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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