Although the chemistry of benzenoid and nonbenzenoid quinones have been
the subject of extensive theoretical and experimental studies, the extent of our
present understanding regarding the geometries and stabilities of quinones of
pentalene is meager. After studying the existence of cyclopentadienone and its
reactivity as a diene and dienophile in the literature, the study of some related
species, particularly the ones with fully unsaturated pentalenic structures were
started.
In this thesis, the elusive compound bicyclo[3.3.0]octa-3,5,8-triene-2,7-dione
was tried to synthesize by using the synthetic strategy which was developed by us.
We used cycloheptatriene as the starting material. The bicyclic
endoperoxiedes mixture obtained by the photooxygenation of cycloheptatriene was
v
treated with triethylamine to give tropone in high yield. Selective reduction of
tropone afforded cyclohepta-3,5-dione which was converted by the way of
photochemistry to the bicyclo[3.2.0]hept-6-en-3-one. After protection of the
carbonyl group, dibromocarbene was added to the double bond to give desired
bicyclic compound with pentalene skeleton. Substitution of the allylic bromide with
hydroxyl group followed by PCC oxidation resulted in the formation of a diketone.
All efforts to convert this diketone into fully conjugated system failed.
| Identifer | oai:union.ndltd.org:METU/oai:etd.lib.metu.edu.tr:http://etd.lib.metu.edu.tr/upload/12605089/index.pdf |
| Date | 01 July 2004 |
| Creators | Atalar, Taner |
| Contributors | Balci, 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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