A comparative synthetic study of a series of six 1,2,3,4,5-pentaphenyl-2,4-cyclopentadiene alkyl ethers was investigated. It was determined that the most efficient route to these ethers was not the most generally accepted route to ethers - the Williamson Reaction - but rather a solvolysis reaction between 1-bromo-1,2,3,4,5-pentaphenyl-2,4-cyclopentadiene and the appropriate alcohol.
Thermal rearrangement of the ethers had been expected to rearrange by a [1,5]-sigmatropic shift of the phenyl group in the 1-position to yield the corresponding enol ether. However, this appeared to occur only as a trace in some cases. Rather, the major product of the thermal rearrangements of these ethers was actually the elimination product, the hydrocarbon, 1,2,3,4,5-pentaphenyl-2,4-cyclopentadiene. The elimination is most likely the result of a retro-ene reaction. / Ph. D. / incomplete_metadata
| Identifer | oai:union.ndltd.org:VTETD/oai:vtechworks.lib.vt.edu:10919/49858 |
| Date | January 1987 |
| Creators | Martin, Patricia |
| Contributors | Chemistry, Ogliaruso, Michael A., Bell, Harold M., Mason, John G., Hudlicky, Milos, Wightman, James P. |
| Publisher | Virginia Polytechnic Institute and State University |
| Source Sets | Virginia Tech Theses and Dissertation |
| Detected Language | English |
| Type | Dissertation, Text |
| Format | xii, 186 leaves, application/pdf, application/pdf |
| Rights | In Copyright, http://rightsstatements.org/vocab/InC/1.0/ |
| Relation | OCLC# 19736982 |
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