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Microwave‐Assisted [4+2] Diels–Alder Cycloaddition of 1,4‐Diethynyl Triptycene with Various Cyclopentadienone Derivatives: Promising Building Blocks for Polymer Networks
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2017-12-20 , DOI: 10.1002/ajoc.201700655
Bassam Alameddine 1 , Noorullah Baig 1 , Suchetha Shetty 1 , Fakhreia Al-Sagheer 2 , Saleh Al-Mousawi 2
Affiliation  

Triptycene derivatives substituted at their 1,4‐ positions with tetraphenylbenzene and diphenyltriphenylene moieties were prepared by microwave‐assisted [4+2] Diels–Alder cycloaddition reactions in very good yields. The target compounds were characterized by 1H and 13C NMR spectroscopy, HRMS, UV/Vis and emission spectrophotometry. In addition, single crystal XRD spectra for two of these derivatives are presented. The tetra‐ and octabrominated triptycene compounds underwent palladium‐catalyzed Suzuki–Miyaura cross‐coupling reactions affording the desired products in very good yields. This successful tetra‐ and octa‐fold substitution paves the way for the employment of these building blocks to prepare polymer networks for various applications.

中文翻译:

微波辅助的[4 + 2] Diels-Alder环加成反应与各种环戊二烯酮衍生物的1,4-二乙炔基三萜烯:聚合物网络的有前途的构建基块

通过微波辅助的[4 + 2] Diels-Alder环加成反应制备了在1,4-位上被四苯苯和二苯基三亚苯基取代的三苯并茂衍生物,收率很高。目标化合物通过1 H和13 C NMR光谱,HRMS,UV / Vis和发射光谱进行表征。此外,还给出了其中两个衍生物的单晶XRD光谱。四溴和八溴三萜化合物经过钯催化的Suzuki-Miyaura交叉偶联反应,可以非常高的收率得到所需的产物。这种成功的四倍和八倍取代为使用这些构件为各种应用制备聚合物网络铺平了道路。
更新日期:2017-12-20
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