Medium-dependent regioselectivity of electrochemical bromination of methyl levulinate†

Dmitry A. Pirgach, Raghavendra Meena, Guanna Li, Fedor M. Miloserdov, Daan S. van Es, Pieter C. A. Bruijnincx and Johannes H. Bitter
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Abstract

An electrochemical method for the bromination of renewable methyl levulinate using ammonium bromide is reported. Regioselectivity depended on the solvent used: the formation of 5-bromolevulinate was favored in methanol and 3-bromolevulinate in a MeCN : H2O mixture. To explain the observed change, different bromination mechanisms were proposed.

乙酰丙酸甲酯电化学溴化的介质依赖区域选择性
报道了一种利用溴化铵进行可再生乙酰丙酸甲酯溴化反应的电化学方法。区域选择性取决于所使用的溶剂:在甲醇中有利于5-溴甲基戊酸酯的形成,而在MeCN: H2O混合物中有利于3-溴甲基戊酸酯的形成。为了解释观测到的变化,提出了不同的溴化机制。
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