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利用苄氯和取代苄氯与叠氮化钠的亲核取代反应合成了一系列苯环上带有不同取代基团的苄基叠氮化合物 ,亲核取代反应速率受苯环上取代基的影响 :吸电子基团的存在 ,可以促使反应更容易进行 .合成的叠氮化合物与苯乙炔经 1,3 偶极环加成反应得到了相应的取代苄基 1,2 ,3 三唑类化合物 ,反应条件温和 .这些 1,2 ,3 三唑类目标化合物具有对热稳定的优点 .用红外、核磁、元素分析、质谱等对合成的叠氮化合物和 1,2 ,3 三唑类化合物的结构进行了表征 ,重点研究了 1,3 环加成反应的规律 .加成反应速率取决于叠氮化合物 (偶极物 )的极性 ,即与取代基的电负性有关 :苯乙炔 (亲偶极物 )易于与缺电子的叠氮反应 ,反之亦然 .同时在反应过程中观察到空间位阻效应 :反应可以生成两种同分异构体 ,其中 4 苯基 1,2 ,3 三唑是主要产物
A series of benzyl azide compounds with different substituents on benzene rings were synthesized by the nucleophilic substitution reaction of benzyl chloride and substituted benzyl chloride with sodium azide. The nucleophilic substitution reaction rate was affected by the substituents on the benzene ring : The existence of electron-withdrawing group can promote the reaction more easily.The synthesis of azide and phenylacetylene by 1,3 dipolar cycloaddition affords the corresponding substituted benzyl 1,2, 3 triazole compounds, The reaction conditions are mild.These 1,2,3-triazole target compounds have the advantages of thermal stability.The structures of the synthesized azide compounds and 1,2,3-triazole compounds were characterized by IR, NMR, elemental analysis and mass spectrometry The characterization of the 1,3-ring addition reaction is mainly focused on the reaction of 1,3-addition.The reaction rate depends on the polarity of the azide (dipole), which is related to the electronegativity of the substituents: phenylacetylene Polar) easily react with the electron deficient azide and vice versa, while the steric hindrance effect is observed during the reaction: the reaction can generate two isomers, of which the 4-phenyl-1,2-triazole Is the main product