The Stereochemistry of 1,4-Di-Tert-Butyl-1,4-Dihydronaphthalene

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A new approach was taken in the elucidation of the stereochemistry of the symmetrically 1,4-disubstituted 1,4-dihydronaphthalene systems which show deceptively simple NMR spectra. Thus, the stereochemistry of 1,4-di-tert-butyl-1,4-dihydronaphthalene was established unequivocally. The epoxide derivative, the subject compound, 1,4-di-tertbutyl-2, 3-epoxy-1, 4-dihydronaphthalene, was formed and its trans stereochemistry was established by ¹H NMR and ¹³C NMR. A lanthanide shift study was also conducted on the epoxide derivative, further proving the trans stereochemistry. One of the lanthanide shifted spectra was analyzed using the LAACOON III computer program and the true coupling constants obtained this way were in excellent agreement with the experimental spectrum. ... continued below

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v, 45 leaves: ill.

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McDaniel, Oya A. December 1980.

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  • McDaniel, Oya A.

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A new approach was taken in the elucidation of the stereochemistry of the symmetrically 1,4-disubstituted 1,4-dihydronaphthalene systems which show deceptively simple NMR spectra. Thus, the stereochemistry of 1,4-di-tert-butyl-1,4-dihydronaphthalene was established unequivocally. The epoxide derivative, the subject compound, 1,4-di-tertbutyl-2, 3-epoxy-1, 4-dihydronaphthalene, was formed and its trans stereochemistry was established by ¹H NMR and ¹³C NMR. A lanthanide shift study was also conducted on the epoxide derivative, further proving the trans stereochemistry. One of the lanthanide shifted spectra was analyzed using the LAACOON III computer program and the true coupling constants obtained this way were in excellent agreement with the experimental spectrum. Establishing the trans stereochemistry of the epoxide derivative proved the trans stereochemistry of 1,4-di-tert-butyl-1,4-dihydronaphthalene.

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v, 45 leaves: ill.

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  • December 1980

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  • May 10, 2015, 6:16 a.m.

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McDaniel, Oya A. The Stereochemistry of 1,4-Di-Tert-Butyl-1,4-Dihydronaphthalene, thesis, December 1980; Denton, Texas. (digital.library.unt.edu/ark:/67531/metadc504433/: accessed October 19, 2018), University of North Texas Libraries, Digital Library, digital.library.unt.edu; .