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旋光活性O-乙基O-苯基硫代磷酰氯在碱存在下与伯胺、仲胺或氨反应,得到构型翻转的O-乙基O-苯基硫代磷酰胺.其酸性水解在6 mol/L或9 mol/L盐酸/二氧六环中进行,得P—N键断裂的构型翻转产物;碱性水解在1 mol/L或3 mol/L NaOH/二氧六环中进行,得到以OPh为离去基团的构型翻转产物.水解反应机理用三角双锥(TBP)中间体概念得到合理解释.
The optically active O-ethyl O-phenylthiophosphoryl chloride is reacted with a primary amine, secondary amine or ammonia in the presence of a base to provide O-ethyl O-phenyl phosphorothioamide of reversed configuration. The acidic hydrolysis of 6 mol / L or 9 mol / L hydrochloric acid / dioxane, resulting in a reversed configuration of the P-N bond; basic hydrolysis in 1 mol / L or 3 mol / L NaOH / dioxane , Resulting in the product with OPh as leaving group.The hydrolysis reaction mechanism was explained by the concept of triangular double cone (TBP) intermediate.