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A detailed study on the ester alkyl exchange reaction of various types of quinique-valent phosphorus esters with alkyl halide in the presence of sodium bromides was reported. This ester alkyl exchange reaction was evidently influenced by the structure of phosphorus esters and alkyl halides as well as by the nature of the halides of metal ions. In contrast with the reaction without sodium hadlide, the alkyl phosphinmate is more reactive than phosphonate and phosphate by treatment with alkyl halide in the presence of sodium halide. This is consistent with the high nucleophilicity of >P(CO)O- as leaving group. The reactivity of butyl halides was decreased in the following order: n-BuBr>i-BuBr=s-BuBr>t-BuBr. Alkyl iodide was proved to be more reactive than the corresponding bromide and chloride. However, the use of iodioe is limited by the formation of alkene resulted from the elimination of HI. These structural effects show the general characteristics of a nucleophilic substitution reaction. A reaction mechanism involving the formation of sodium salt intermecutiate was proposed based on the concept of HSAB principle. This reaction may, however, be used as a convenient method for the preparation of mixed esters of quinque-valent phosphorus acids. 相似文献
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1,1-二卤代-1-烯烃是有机化学中常见的合成片断,在合成化学中已得到了广泛的应用。该综述介绍了这一类化合物常见的制备方法以及反应的适用范围,并详细讨论了该类化合物在有机合成中的应用:(1)1,1-二卤代-1-烯烃在镁、有机锂、锌/溴化亚铜、二碘化钐、零价钯等金属或金属试剂作用下,发生α-消除反应生成烯基卡宾中间体的反应;(2)1,1-二卤代-1-烯烃在合成杂环以及核苷类似物等方面的应用。对于这类化合物在钯催化下的分子内(间)的偶联反应以及利用分子内的双环碳钯化反应,合成环状化合物等等方面的研究进展,也进行了详细的讨论。 相似文献
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