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Synthesis of Bis-anthranone Derivates and the Acid Catalytic Selective Reaction of Reduction Products

Author: JiangXiaoQian
Tutor: CaoDeZuo
School: South China University of Technology
Course: Applied Chemistry
Keywords: triptycene homotriptycene bishomotriptycene bisanthrone anthracene derivative
CLC: TQ203.2
Type: Master's thesis
Year: 2011
Downloads: 19
Quote: 0
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Abstract


Triptycene and its derivatives are a class of structurally unique compounds consisting of arenes that are fused together through the bicyclo[2.2.2]octane framework. The triptycenes, due to their special structure and unique electrochemical and photochemical properties, have been found versatile usages in constructing molecules of both fundamental and practical importance. Homotriptycene is a class of important homologous compound of triptycene. Compared with the developed research of triptycene, the study on homotriptycene is so limited that no literature of bis-or multiple- homotriptycene can be found yet.On the basis of previous research, several synthetic routes are designed in order to achie- ve expected target. Herein, bisanthrone derivatives were synthesized starting from anthrone thhrough condensation, Pd/C hydrogenation and Williamson alkylation reaction. After reduc- tion by NaBH4 in diglyme with microwave irradiation, a selective 1,7-dehydrationcyclization reaction gave 10,10’-(p-xylylene)-bishomotriptycenes in quantitative yields with acid as cat- alyst.The results show that the acid-catalyzed reaction of reduction products of bisanthrone (bisanthranol) are complex and existe a variety of competitive responses. Influenced by the substituents in benzene ring, 10,10’-(p-xylylene)-bishomotriptycenes were successfully synth- esized starting from compounds 3-1f~g with reduction and subsequent 1,7-dehydration -cyclization reaction. However, under the same conditions, 2-10d~e and 3-1h respectively reacted with 1,4-dehydration and rearrangement reaction to give novel bisanthracene derivatives instead of expected bishomotriptycenes. In view of the good specificity and high yields, this method can be used to synthesize bisanthracene derivatives with novel and symmetrical structure in a good way. It also can be lay a solid foundation for the photoch- emical reaction of anthracene derivatives in the next step. In addition, novel anthracene derivatives such as endoperoxides of anthranol and ketonic-enolic type symbiotic compounds were also obtained as by-products.Herein, 18 new compounds were synthesized and characterized. Unfortunately, limited by time, several synthetic routes havn’t been attempted yet.

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