摘要
在固液相转移催化（Ｋ_２ＣＯ_３／ＤＭＦ／ＴＥＢＡ）条件下，对硝基苯磺酰基乙酸酯与α，β－不饱和酸酯反应意外地生成加成重排产物［如生成２－甲基－２－（对硝基苯基）戊二酸－１－甲酯－５－乙酯］。其反应机理可能是砜酯首先与α，β－不饱和酯起Ｍｉｃｈａｅｌ反应，随后加成物发生分子内芳环上的亲核性取代，酸化后脱去ＳＯ２得最终产物。
The reaction of p-nitrophenylsulfonylacetate with α,β-unsaturated esters under solid-liquid phase transfer conditions (K2CO3/DMF/TEBA) gave the unexpected Michael addition-rearrangement products, For example, the reaction of pnitrophenylsulfonylacetate with methyl methacrylate resulted in the formation of 2-methyl-2-(p-nitrophenyl) glutarate, presumably through the Michael adduct, which might rearrange to an intermediate, furtherlose sulfur dioxide and then led to the final product.
出处
《高等学校化学学报》
CSCD
北大核心
1995年第9期1410-1414,共5页
Chemical Journal of Chinese Universities
关键词
对硝基苯
磺酰基
乙酸酯
不饱和酸酯
加成反应
p-Nitrophenylsulfonylacetate
α
β-unsaturated ester
Solid-liquid phase-transfer catalysis
Michael addition
