Investigation of the synthesis and thermal rearrangements of 1,2,3,4,5-Pentaphenyl-2,4,-Cyclopentadiene Alkyl Ethers

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.

Name thesis:degree_name

Ph. D.

Level thesis:degree_level

doctoral

Discipline thesis:degree_discipline

Chemistry

Department dc:contributor.department

Chemistry

Grantor dc:publisher

Virginia Polytechnic Institute and State University

Year dc:date.issued

1987

Author dc:creator

• Martin, Patricia

Chair dc:contributor.committeechair

• Ogliaruso, Michael A.

Committee members dc:contributor.committeemember

• Bell, Harold M.
• Mason, John G.
• Hudlicky, Milos
• Wightman, James P.

Statement dc:rights

• In Copyright

Licence dc:rights.uri

• http://rightsstatements.org/vocab/InC/1.0/

Handle dc:identifier.uri

http://hdl.handle.net/10919/49858

OAI identifier oai:identifier

oai:vtechworks.lib.vt.edu:10919/49858