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含能材料  2015 

五环[5.4.0.02,6.03,10.05,9]十一烷的合成和表征

DOI: 10.11943/j.issn.1006-9941.2015.02.003

Keywords: [2+2]环加成反应 五环[5.4.0.02,6.03,10.05,9]十一烷 合成

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Abstract:

将二聚环戊二烯裂解生成的环戊二烯, 与对苯二醌进行Diels-Alder加成反应, 得到了1, 4, 4a, 8a-四氢-1, 4-桥亚甲基萘-5, 8-二酮, 经[2+2]环加成和黄鸣龙还原反应, 最终得到目标产物五环[5.4.0.02,6.03,10.05,9]十一烷, 产物总收率为51.6%, 采用熔点测定、核磁共振氢谱、碳谱、红外光谱和质谱对各步产物进行了表征。探讨了Diels-Alder加成和[2+2]环加成反应的影响因素, 确定了Diels-Alder加成反应的最佳反应条件:滴加环戊二烯时溶液温度-11 ℃, 时间3 h。[2+2]环加成反应的最佳条件是:以丙酮做溶剂, 原料浓度2 g·125mL-1, 光照时间23 h

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