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.
| Identifer | oai:union.ndltd.org:unt.edu/info:ark/67531/metadc504433 |
| Date | 12 1900 |
| Creators | McDaniel, Oya A. |
| Contributors | Marshall, James L., 1940-, Daugherty, Kenneth E., Beller, Nicholas R. |
| Publisher | North Texas State University |
| Source Sets | University of North Texas |
| Language | English |
| Detected Language | English |
| Type | Thesis or Dissertation |
| Format | v, 45 leaves: ill., Text |
| Rights | Public, McDaniel, Oya A., Copyright, Copyright is held by the author, unless otherwise noted. All rights reserved. |
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