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Ishikawa试剂(石川试剂)能将伯醇,仲醇和叔醇转化为相应的氟化合物,对羰基没有影响。其中伯醇反应性能比较好,仲醇和叔醇会有消除或偶联的副产物产生。反应通常在乙醚或二氯甲烷中进行。
用Ishikawa试剂氟代条件比较温和,选择性也很好,如下面这个分子的全合成中,环氧,双键和保护基都没被破坏。

反应实例

To a solution of Ishikawa reagent (3 g, 13.5 mmol) in dry dichloromethane (30 mL), a solution of 3-nitrobenzyl alcohol (1.5 g, 9.6 mmol) in dichloromethane (10 ml) vas added dropvise at room temperature. After stirring for 6 h, the reaction mixture vas left overnight. It vas then poured into water and the oily product vas extracted with diisopropyl ether. The ether extract vas washed with water, dried over anhydrous sodium carbonate, filtered, and evaporated to remove the solvent. The residue was distilled to give the desired product (1 g, 48%).
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