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化学学报
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化学学报 ›› 2010, Vol. 68 ›› Issue (20): 2069-2076. 上一篇    下一篇

研究论文

对苯二亚甲基联二高三蝶烯的合成

蒋晓乾，李志云，曹德榕   

  1. (华南理工大学化学与化工学院 广州 510640)
  • 投稿日期:2010-05-10 修回日期:2010-06-16 发布日期:2010-06-28
  • 通讯作者: 曹德榕 E-mail:drcao@scut.edu.cn
  • 基金资助:

    国家自然科学基金项目

Synthesis of 10,10 -(p-Xylylene)-bishomotriptycenes

JIANG Xiao-Qian, LI Zhi-Yun, CAO De-Rong   

  1. (School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640)
  • Received:2010-05-10 Revised:2010-06-16 Published:2010-06-28
  • Contact: Derong Cao E-mail:drcao@scut.edu.cn

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3638

被引次数

10

报道了一种从蒽酮出发制备对苯二亚甲基联二高三蝶烯的合成方法. 以蒽酮为原料, 经缩合、加氢还原以及Williamson烷基化反应得到一系列的联二蒽酮衍生物10e, 12f～12h. 受其10位取代基等因素的影响, 12f～12g在NaBH4还原和酸催化条件下发生选择性的1,7-跨环脱水成环反应, 高产率地得到了联二高三蝶烯14f～14g. 在相同条件下, 10e和12h却发生了1,4-脱水和重排反应生成了联二蒽衍生物15i～15j, 而不是预期的螺环类联二高三蝶烯产物16i～16j. 另外, 在制备过程中还得到了一些结构新颖的副产物如蒽醇过氧化物5a～5c, 以及蒽醚酮类衍生物11a, 13a等.

关键词: 三蝶烯, 高三蝶烯, 联二高三蝶烯, 联二蒽酮, 蒽醇过氧化物, 蒽

10,10 -(p-Xylylene)-bishomotriptycenes 14f～14g were prepared from bisanthrone derivatives 12f～12g. Bisanthrone derivatives were synthesized starting from anthrone through condensation, Pd/C hydrogenation and Williamson alkylation reactions. Reduction of 12f～12g by NaBH4 in diglyme with microwave irradiation and subsequently a selective 1,7-dehydration-cyclization reaction with acid as catalyst gave bishomotriptycenes 14f～14g in quantitative yields. However, reduction of 10e, 12h and subsequently 1,4-dehydration and rearrangement reaction gave two novel bisanthracene derivatives 15i～15j instead of expected bishomotriptycenes 16i～16j. In addition, novel anthracene derivatives 11a, 13a and endoperoxides 5a～5c were also obtained as by-products.

Key words: triptycene, homotriptycene, bishomotriptycene, bisanthrone, endoperoxide, anthracene