Insertion of Fischer Carbene Complexes into the Carbon-Carbon Bond of 1,2-Diphenylcyclopropenone: Formation of Cyclobutenones and o- and p-Methoxyphenol Derivatives

Date

1994-08-01

Author

Zora, Metin

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

138
views

0
downloads

Thereactionbetween1,2-diphenylcyclopro-penoneandFischercarbenecomplexeshasbeeninves-tigated.Thereactionproducedamixtureofdipheny-lacetyleneandcyclobutenones.Whena,ß-unsaturatedcarbenecomplexeswereemployed,benzannulationprod-uctsanddiphenylacetylenewereproduced.Amecha-nisminvolvingmetallacyclobutenoneformation,followedbyeithercarbeneinsertionandreductiveeliminationorfragmentationhasbeenproposed.Recently,wereportedthatcarbon—carbonbondin-sertionisthemajorreactionpathwaywhenFischercarbenecomplexesreactwith1,2-cyclobutenediones,1affording4-cyclopentene-l,3-dionesand/or5-alkylidene-furanones.Otherstrainedringsmightleadtoinsertionproductsaswell.Avarietyofadditionalringsystemsweretestedinthisreaction,includingcyclobutenones,cyclobutenes,cyclopropanes,cyclopentadienones,andcyclopropenones.Ofthese,onlythecyclopropenoneringsystemaffordedcarbon—carbonbondinsertionproductswhentreatedwithFischercarbenecomplexes.Hereinwereportthereactionbetween1,2-diphenylcyclopro-penoneandFishercarbenecomplexes.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry

URI

https://hdl.handle.net/11511/36332

Journal

Organometallics

DOI

https://doi.org/10.1021/om00020a059

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis, characterization, and electrochemistry of tetracarbonyl(6-ferrocenyl-2,2 '-bipyridine)tungsten(0) Edinc, Pelin; Oenal, Ahmet M.; Özkar, Saim (Elsevier BV, 2007-04-15) 6-Ferrocenyl-2,2'-bipyridine (fcbpy) was prepared by the reaction of lithiated ferrocene with bipyridine and employed as a bidentate ligand for the formation of tetracarbonyl(6-ferrocenyl-2,2'-bipyridine)tungsten(0). The labile complex pentacarbonyl[eta(2)-bis(trimethylsilyl)ethyne]tungsten(0) reacts with fcbpy in CH2Cl2 to yield the disubstitution product, W(CO)(4)(fcbpy), which was isolated as analytically pure substance and characterized by elemental analysis, IR, UV-Vis, MS, H-1 and C-13 NMR spectroscop...
Selective recognition of anionic cell membranes using targeted liposomes coated with zinc(II)-bis(dipicolylamine) affinity units Türkyılmaz, Serhan; Palumbo, Rachael; Smith, Bradley D. (Royal Society of Chemistry (RSC), 2014-08-14) Zinc(II)-bis(dipicolylamine) (Zn(2)BDPA) coated liposomes are shown to have high recognition selectivity towards vesicle and cell membranes with anionic surfaces. Robust synthetic methods were developed to produce Zn(2)BDPA-PEG-lipid conjugates with varying PEG linker chain length. One conjugate (Zn(2)BDPA-PEG(2000)-DSPE) was used in liposome formulations doped with the Lipophilic near-infrared fluorophore DiR. Fluorescence cell microscopy studies demonstrated that the multivalent Liposomes selectively and ...
Dipole moments of some styrene copolymers Küçükyavuz, Zühal; Baysal, Bahattin (American Chemical Society (ACS), 1988-7) Dipolemomentsofpoly(styrene-co-p-chlorostyrene),poly(styrene-co-p-methoxystyrene),poly(styrene-co-4-vinylpyridine),andpoly(styrene-co-N-vinylcarbazole)copolymersweredeterminedintoluenesolutionsatdifferenttemperatures.Thesamplesweresynthesizedbyusingfree-radicalinitiators.Theeffectsofthenatureofthepolargroup,composition,andtemperatureonthedipolemomentratiowereinvestigated.Themean-squaredipolemomentperstructuralunitshowsapositivedeviationfromlinearity,inagreementwithcalculationsbyMarkbasedonrotationalisomeric...
Ruthenium(III) acetylacetonate: A homogeneous catalyst in the hydrolysis of sodium borohydride Keceli, Ezgi; Özkar, Saim (Elsevier BV, 2008-05-01) Ruthenium(ill) acetylacetonate was employed for the first time as homogeneous catalyst in the hydrolysis of sodium borohydride. Ruthenium(III) acetylacetonate was not reduced by sodium borohydride under the experimental conditions and remains unchanged after the catalysis. Poisoning experiments with mercury and trimethylphosphite provide compelling evidence for the fact that ruthenium(III) acetylacetonate is indeed a homogenous catalyst in the hydrolysis of sodium borohydride. Kinetics of the ruthenium(III)...
CONDUCTIVE PROPERTIES OF POLY(4-VINYLPYRIDINE) POLY(DIMETHYLSILOXANE) BLOCK-COPOLYMERS DOPED WITH TETRACYANOQUINODIMETHANE NUGAY, N; KUCUKYAVUZ, Z; KUCUKYAVUZ, S (Elsevier BV, 1993-01-01) Poly(4-vinylpyridine)-poly(dimethylsiloxane) (P4VP-PDMS) block copolymers with various compositions were prepared by anionic polymerization. The 4VP block was quaternized with methyl iodide and reacted with 7,7',8,8'-tetracyanoquinodimethane (TCNQ), which is in both anion radical (TCNQ-.) and neutral form (TCNQ0). The products were then characterized by H-1 nuclear magnetic resonance and Fourier-transform infra-red spectroscopy, scanning electron microscopy and differential scanning calorimetry techniques. ...

Citation Formats

M. Zora, “Insertion of Fischer Carbene Complexes into the Carbon-Carbon Bond of 1,2-Diphenylcyclopropenone: Formation of Cyclobutenones and o- and p-Methoxyphenol Derivatives,” Organometallics, pp. 3370–3373, 1994, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/36332.