Synthesis and Conformational Studies of Some Metacyclophane Compounds

Louis Korbla Doamekpor, Vincent Kodzo Nartey, Raphael Kwaku Klake, Takehiko Yamato

Department of Chemistry, University of Ghana, Accra, Ghana.
epartment of Chemistry, Saga University, Saga, Japan.

DOI: 10.4236/ijoc.2012.22023                

Abstract

Various [3.3.3]metacyclophane derivatives were synthesized from 6,15,24-tri-tert-butyl-9,18,27-trimethoxy [3.3.3] metacyclophane-2,11,20-trione 1 using simple chemical reactions. The conformations of the synthesized compounds were studied using mainly solution Proton Nuclear Magnetic Resonance (1H NMR) spectroscopic methods. Two of the synthesized compounds 5, 6, were found to have a partial cone conformation with the third, 4, having the cone conformation. Detailed variable temperature Proton Nuclear Magnetic Resonance studies further confirmed the partialcone conformation for the two products, 5, 6. During the variable temperature nuclear magnetic resonance spectroscopic studies, 6,15,24-tri-tert-butyl-9,18,27-trimethoxy[3.3.3]metacyclophane-2,11,20-triol was found to have a coalescence temperature of about 0?C.

Keywords

Metacyclophanes; Calixarenes; Cone; Partial-Cone; Conformers; Variable Temperature Proton Nuclear Magnetic Resonance Spectroscopy; Coalescence Temperature

Conflicts of Interest

The authors declare no conflicts of interest.

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