International Journal of Organic Chemistry

Volume 2, Issue 2 (June 2012)

ISSN Print: 2161-4687   ISSN Online: 2161-4695

Google-based Impact Factor: 1.26  Citations  

Synthesis and Conformational Studies of Some Metacyclophane Compounds

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DOI: 10.4236/ijoc.2012.22023    4,484 Downloads   7,998 Views  Citations

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.

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L. Doamekpor, V. Nartey, R. Klake and T. Yamato, "Synthesis and Conformational Studies of Some Metacyclophane Compounds," International Journal of Organic Chemistry, Vol. 2 No. 2, 2012, pp. 152-158. doi: 10.4236/ijoc.2012.22023.

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