Synthetic strategy directed towards the synthesis of bicyclo[3.3.0]octa-3,5,8-triene-2,7-dione

Download

index.pdf

Date

2004

Author

Atalar, Taner

Metadata

Show full item record

Item Usage Stats

148
views

73
downloads

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.

Subject Keywords

Aromatic compounds.

URI

http://etd.lib.metu.edu.tr/upload/12605089/index.pdf
https://hdl.handle.net/11511/14246

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

Generation of aryl radicals from arylboronic acids by manganese(III) acetate: Synthesis of biaryls and heterobiaryls Demir, Ayhan Sıtkı; Reis, O; Emrullahoglu, M (2003-01-24) The efficient generation of aryl radicals from arylboronic acids by manganese(III) acetate is described. In aromatic solvents, in situ generated aryl radicals afford the corresponding biaryls in very good yields. This method works selectively, and yields are better than those from similar, previously described methods. Arylboronic acids carrying sensitive functional groups also work efficiently.
Development of new methods for the synthesis of pyrazoles, 4-iodopyrazoles, isoxazoles and 1,2,4-oxadiazoles Kıvrak, Arif; Zora, Metin; Department of Chemistry (2011) Synthesis of five-membered heteroaromatic compounds such as pyrazoles, isoxazoles and 1,2,4-oxadiazoles are important for pharmaceutical industry and material science due to their applications. Although there are many methods to prepare such compounds, new variants continue to appear since they exhibit a wide range of biological and medicinal activities. In this thesis, new methods were developed for the synthesis of 4-iodopyrazoles, pyrazoles, isoxazoles, 1,2,4-oxadiazoles and/or 1,2,4-oxadiazepines. In th...
Ni-MCM-41 type mesoporous catalysts synthesized by one-pot hydrothermal procedure for steam reforming of ethanol Ozdogan, Ekin; Doğu, Timur; DOĞU, GÜLŞEN (2007-01-02) In the present study, Ni incorporated MCM-41 structured mesoporous catalysts with a Ni/Si atomic ratio of 0.036 and 0.15 were prepared by a direct hydrothermal synthesis procedure. These catalysts had surface area values of 860.5 m(2)/g (Ni-MCM-41 having a Ni/Si ratio of 0.036) and 944.9 m(2)/g (Ni-MCM-41 having a Ni/Si ratio of 0.15). They also had narrow pore size distributions with average pore diameters of 2.7-2.6 nm respectively. Ni MCM-41 synthesized by the one-pot hydrothermal synthesis procedure sho...
Studies towards synthesis of urea containing helical polymers Çalışgan, Gizem; Akdağ, Akın; Doğan, Özdemir; Department of Chemistry (2016) This thesis deals with design and synthesis of chiral polyurea type polymers. These polymers were analyzed with molecular mechanics that they could take a helical form. The polymers are polyurea type polymers and ureas are synthesized by treating isocyanates with amines. Starting from tartaric acid, ((4S,5S)-2,2-dimethyl-1,3- dioxolane-4,5diyl)dimethaneamine was synthesized. The other diamine was naturally occuring L-lysine. These diamine functionalized compounds were treated with pphenylene diisocyanate sy...
Novel conversion of thiols into disulfides, via S-nitrosothiol intermediates using trichloronitromethane Demir, Ayhan Sıtkı; Igdir, AC; Mahasneh, AS (1999-10-15) An efficient oxidative coupling of thiols to give disulfides via thionitrite (S-nitrosothiol) intermediate is described using trichloronitromethane as an efficient reagent in organic solvents and water. Cysteine and glutathione are converted into the corresponding disulfides in water in high yields.

Citation Formats

T. Atalar, “Synthetic strategy directed towards the synthesis of bicyclo[3.3.0]octa-3,5,8-triene-2,7-dione,” M.S. - Master of Science, Middle East Technical University, 2004.