Recently, considerable interest has been devoted to the synthesis of new
ferrocene derivatives since properly functionalized ferrocene derivatives could be
potential antitumor substances. For this purpose, we have investigated the synthesis
of ferrocenyl quinones starting from squaric acid. Thermolysis of ferrocenylsubstituted
cyclobutenones, which have been prepared from ferrocenyl
cyclobutenediones and alkenyllithiums, affords hydroquinones, which furnish, upon
oxidation, ferrocenyl quinones. Ferrocenyl cyclobutenediones have been prepared
from known cyclobutenediones by nucleophilic addition of
ferrocenyllithiumfollowed by hydrolysis, Pd/Cu-cocatalyzed cross-coupling with
(tri-n-butylstannyl)ferrocene or Friedel& / #8211 / Crafts alkylation with ferrocene. A
mechanism involving electrocyclic ring opening of alkenyl substituted
cyclobutenone to dienylketene and consequent electrocyclic ring closure to
cyclohexadienone followed by enolization has been proposed to account for the
formation of ferocenyl substituted hydroquinones.
Rocket design and production is one of the hottest topics in defense industry.
On this subject, significant amount of investments have been done and excellent
results were obtained. Among the burning rate catalysts for composite rocket
propellants, ferrocene derivatives are one of the most famous ones. Although
ferrocene derivatives are superior to some other burning rate catalysts, their use has
some drawbacks arising from the tendency of migration in the bulk of the material
and their sensitivity toward oxidation by air. With the aim of preventing the negative
aspects of ferrocene derivatives, we have investigated the synthesis of EDA
(ethylenediamine), TEP (tetraethylenepentamine) and DDI (dimeryl-diisocyanate)
based ferrocene derivatives.
| Identifer | oai:union.ndltd.org:METU/oai:etd.lib.metu.edu.tr:http://etd.lib.metu.edu.tr/upload/1081256/index.pdf |
| Date | 01 January 2003 |
| Creators | Acikalin, Serdar |
| Contributors | 105, Zora Metin |
| Publisher | METU |
| Source Sets | Middle East Technical Univ. |
| Language | English |
| Detected Language | English |
| Type | M.S. Thesis |
| Format | text/pdf |
| Rights | To liberate the content for public access |
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