Acta Chimica Sinica ›› 2010, Vol. 68 ›› Issue (20): 2069-2076. Previous Articles     Next Articles

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  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
  • 基金资助:


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

10,10 -(p-Xylylene)-bishomotriptycenes 14f14g were prepared from bisanthrone derivatives 12f12g. Bisanthrone derivatives were synthesized starting from anthrone through condensation, Pd/C hydrogenation and Williamson alkylation reactions. Reduction of 12f12g by NaBH4 in diglyme with microwave irradiation and subsequently a selective 1,7-dehydration-cyclization reaction with acid as catalyst gave bishomotriptycenes 14f14g in quantitative yields. However, reduction of 10e, 12h and subsequently 1,4-dehydration and rearrangement reaction gave two novel bisanthracene derivatives 15i15j instead of expected bishomotriptycenes 16i16j. In addition, novel anthracene derivatives 11a, 13a and endoperoxides 5a5c were also obtained as by-products.

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