A new, efficient route was used in the synthesis of [2.2]-paracyclophane-2-carboxylic acid. The acid as then resolved and the Birch reduction performed yielding one enantiomer of tetrahydro-[2.2]-paracyclophane-2-carboxylic acid. The ultraviolet spectrum of tetrahydro-[2.2]-paracyclophane- 2-carboxylic acid in isopenthane shows one absorption at 206 nm (Emax = 5,271). There are three bands observed in the circular dichroism spectrum in isopentane at 236 nm ([] = 1.8 X 104), 201 nm ([0] = -16 X 104) and a positive band indicated below 180 nm but not observed. The bands were assigned and possible reasons for the occurrence of a mr'r* transition at unexpectedly long wavelengths are discussed.
| Identifer | oai:union.ndltd.org:unt.edu/info:ark/67531/metadc504545 |
| Date | 05 1900 |
| Creators | Hall, Lindsey |
| Contributors | Marshall, James L., 1940-, Desiderato, Robert, Russell, Benny |
| Publisher | North Texas State University |
| Source Sets | University of North Texas |
| Language | English |
| Detected Language | English |
| Type | Thesis or Dissertation |
| Format | v, 51 leaves: ill., Text |
| Rights | Public, Hall, Lindsey, Copyright, Copyright is held by the author, unless otherwise noted. All rights reserved. |
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