Synthesis of ferrocenyl cyclopentenones

Download

index.pdf

Date

2005

Author

Tumay, Tülay Aslı

Metadata

Show full item record

Item Usage Stats

90
views

68
downloads

Construction of highly functionalized five-membered rings via cycloaddition reaction of cyclopropylcarbene-chromium complex with alkynes has become a very active area of research in recent years by virtue of their presence in antitumour natural products. Also with the finding that ferrocene derivatives are active against various tumours, considerable interest has been devoted to the synthesis of new ferrocene derivatives since properly functionalized ferrocene derivatives could be potential antitumour substances. So, the incorporation of the essential structural features of cyclopentenones with a ferrocene moiety could provide compounds with enhanced antitumour activities. For this purpose, we have investigated the reaction between cyclopropylcarbene-chromium complex and ferrocenyl alkynes. The reaction of cyclopropylcarbene-chromium complex with ferrocenyl alkynes afforded ?-hydroxycyclopentenones in a one-pot process, whereas the same reaction with alkynes gave cyclopentenones as major products. Interestingly, water addition was observed instead of reduction according to the previously proposed mechanism. This is a different result than those in literature. The reaction was regioselective both with terminal ferrocenyl alkynes and internal unsymmetrical ferrocenyl alkynes. The products obtained were those where the sterically larger alkyne substituent, ferrocene, was ? to the carbonyl group.

Subject Keywords

Organometallic chemistry.

URI

http://etd.lib.metu.edu.tr/upload/3/12606372/index.pdf
https://hdl.handle.net/11511/15268

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

Synthesis and characterization of tetracarbonyl(6-ferrocenyl-2.2'-bibyridine)tungsten(0) complex Edinç, Pelin; Özkar, Saim; Department of Chemistry (2005) In this study, a bidentate ligand, 6-ferrocenyl-2,2'-bipyridine, was prepared by the reaction of lithiated ferrocene with bipyridine. The ligand was identified by 1H, 13C- NMR and HMQC and UV-Vis spectroscopies. Then, bidentate molecule was reacted with pentacarbonylbis-(trimethylsilylethyne)tungsten(0). The ligand substitution reaction in CH2Cl2 yielded the new complex, tetracarbonyl(6-ferrocenyl-2,2'bipyridine)tungsten(0). The isolated and purified complex was fully characterized by elemental analysis, IR...
Synthesis of 2-aziridinyl phosphonates by modified Gabriel-Cromwell reaction and their antibacterial activities Doğan, Özdemir; Gözen, Ayşe Gül (Elsevier BV, 2011-06-01) A set of new aziridinyl phosphonates (4a-g) were synthesized by using the Gabriel-Cromwell reaction and its modified version developed in this study and their structures confirmed by HRMS, IR. and NMR spectra. All the compounds were screened for their antibacterial activity. They all showed comparable moderate to good growth inhibitory activity in reference to ampicillin and streptomycin. (C) 2011 Elsevier Masson SAS. All rights reserved.
Synthesis of ferrocenyl quinolines Zora, Metin (Elsevier BV, 2008-06-01) A convenient one-pot synthesis of ferrocenyl-substituted quinolines via a molecular iodine-catalyzed reaction of ferrocenylimines with enolizable aldehydes is reported. First, nucleophilic addition of the in situ generated enol to ferrocenylimine produces beta-anilinopropionaldehyde, which then undergoes intramolecular Friedel-Crafts reaction to give dihydroquinoline derivative. Finally, subsequent dehydration and aerobic oxidation affords ferrocenyl quinolines.
Synthesis of ferrocenyl cycloheptadienones Açıkgöz, Canet; Zora, Metin; Department of Chemistry (2005) Synthesis of seven-membered ring systems such as cycloheptadienones has attracted a great deal of attention in organic chemistry since they are present in a variety of biologically important molecules. Incorporation of the essential structures of such compounds with a ferrocene moiety instead of an aryl group could provide subtances with enhanced antitumor activities since some ferrocene derivatives have already proved to be active against a number of tumors. To develop a ferrocenyl-substituted seven-member...
Synthesis of conducting polysiloxane-polypyrrole graft copolymers Gunaydin, O; Toppare, Levent Kamil; Yagci, Y; Harabagiu, V; Pintela, M; Simionescu, BC (Springer Science and Business Media LLC, 2002-02-01) Polysiloxane-polypyrrole graft copolymers have been synthesized by a series of chemical reactions and subsequent electropolymerization. First, the hydrosilation of 4-vinyl aniline by dimethyl-methylhydrosiloxane copolymer gave the corresponding aminophenyl functional polydimethylsiloxane (PDMS-NH2). The side chain pyrrole functionalized. polysiloxanes were then prepared by the reaction of PDMS-NH2 with glycidylpyrrole. Finally, the synthesis of graft copolymers of polysiloxane and pyrrole has been achieved ...

Citation Formats

T. A. Tumay, “Synthesis of ferrocenyl cyclopentenones,” M.S. - Master of Science, Middle East Technical University, 2005.