Study of Pinacol Coupling Reaction to Synthesize Functional Macrocyclic Molecules

Abstract

[2.1.2.1]Metacyclophane ([2.1.2.1]MCP) 3 containing hydroxyl groups at the bridge is obtained by a pinacol coupling reaction using aluminum powder. The Albright-Gordman oxidation of [2.1.2.1]MCP 3 yielded tetracarbonyl derivative 4 , and the following condensation reaction of 1,2-phenylenediamine yielded quinoxaline-annulated [2.1.2.1]MCP 5 . The UV and fluorescence spectra as well as the influences of an alkali metal ion on the fluorescence spectra of quinoxaline-annulated [2.1.2.1]MCP 5 were reported

Keywords:

• calixarene
• fluorescence
• metacyclophane
• pinacol coupling
• quinoxaline
• UV-Vis absorption spectrum

Acknowledgments

This work was supported by the Department of Applied Chemistry and Biochemistry, Faculty of Engineering, and Department of Science and Technology for Chemistry and Physics, Graduate School of Science and Technology, Kumamoto University.