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有机化学
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有机化学 ›› 2001, Vol. 21 ›› Issue (3): 235-237. 上一篇    下一篇

研究论文

N-取代环十二酮缩氨基硫脲的氧化环合反应

张振业;金淑惠;梁晓梅;王志强;王道全   

  1. 中国农业大学应用化学系;农药化学及农药使用技术农业部重点开放实验室
  • 发布日期:2001-03-25

Oxidative cyclisation of N-substituted cyclododecanone thiosemicarbazones

Zhang Zhenye;Jin Shuhui;Liang Xiaomei;Wang Zhiqiang;Wang Daoquan   

  • Published:2001-03-25

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被引次数

4

以环十二酮为起始物合成的一系列N-取代环十二酮缩氨基硫脲(Ⅰ)经二氧化锰氧化环合为2-(1,11-十一亚甲基)-5-取代亚氨基-△^3-1,3,4-噻二唑啉(Ⅱ)。Ⅱ的结构得到IR，13^CNMR和元素分析的确证。反应中同时分离到一个副产物，经IR，13^CNMR,EIMS和元素分析确定其结构为2-(1,11-十一亚甲基)-5-亚氨基△^3-1,3,4-噻二唑啉(Ⅲ)。据此提出了Ⅰ经二氧化锰氧化环合为Ⅱ的两步反应机制，此机制可以合理地解释Ⅱ和Ⅲ的生成。

关键词: 环十二酮, 缩氨基硫脲P, 十二员环化合物, 噻二唑啉, 二氧化锰, 氧化反应, 合成法, 环化, 反应机理, 噻二唑P

N-Substituted cyclododecanone thiosemicarbazones Ⅰ, prepared from cyclododecanone, undergo oxidative cyclisation on treatment with manganese dioxide giving 2-(1,11-undecylidene) -5-substituted imino-△ ^3-1,3,4-thiadiazolines Ⅱ. The structures of Ⅱ were confirmed by IR, 13^C NMR and elemental analysis. A by-product was separated from the reaction mixture and its structure was assigned as 2-(1,11- undecylidene)-5-imino- △ ^3-1,3,4-thiadiazoline Ⅲ by IR, 13^C NMR, EIMS and elemental analysis. A two-step reaction mechanism for the oxidative cyclisation of Ⅰ on manganese dioxide was proposed to explain the formation of Ⅱ and Ⅲ.

Key words: THIOSEMICARBAZONE P, DODECAMEMBER RING COMPOUNDS, MANGANESE DIOXIDE, OXIDATION REACTION, SYNTHESIS METHODS, CYCLIZATION, REACTION MECHANISM, THIADIAZOLE P

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