Synthetic study of organic honeycomb structure consisting of a triptycene unit

2015 Fiscal Year Final Research Report

• Project/Area Number: 26670003
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: Kyushu University
• Principal Investigator: SHINDO MITSURU 九州大学, 先導物質化学研究所, 教授 (40226345)
• Co-Investigator(Renkei-kenkyūsha): MATSUMOTO Kenji 九州大学, 先導物質化学研究所, 助教 (20531817)
• Project Period (FY): 2014-04-01 – 2016-03-31
• Keywords: トリプチセン / ハニカム構造 / イノラート / ベンザイン / 連続反応 / 環化付加

Outline of Final Research Achievements

We found a new synthetic method of triptycenes by the reaction of ynolates and arynes. This reaction contained four successive reactions of three cycloadditions and ring-opening of a Dewar anthracene intermediate. The products were obtained by only one operation and had a hydroxy group at C9 and an alkyl group at C10. While the lithium-halogen exchange method for generation of arynes gave low yields, ortho-lithiation was found to result in much better yields. o-Methoxybenzyne was converted into a triptycene in which all the O-function positioned at the same face. Furthermore, the fluorinated triptycene was also successfully obtained. These results become fundamental perception for construction of the honeycomb structure.

Free Research Field

有機合成化学