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A Study On The Reactivity Of Fe3(CO)12 With Substituted Alkynes RCCR’

Posted on:2014-01-14Degree:MasterType:Thesis
Country:ChinaCandidate:L WuFull Text:PDF
GTID:2251330422456323Subject:Chemical Engineering and Technology
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Cyclopentadienone was synthesized by reaction of transition metal clusters withalkyne is a versatile organic chemical raw materials,it is not only an importantcyclopentadiene ligand and a variety of fine chemicals reaction intermediates,but alsodesign synthesis reaction of aromatic compounds premise by diels-alder reaction,it hasbeen a hot spot in the field of transition metal clusters.As transition metal clusters, the preparation for dodecacarbonyltriiron is simple, andthe starting materials are inexpensive. Meanwhile, dodecacarbonyltriiron not onlyinvolved in the reaction and worked as the catalyst precursor,but also acted as carbonmonoxide source for cyclopentadiene ketone which belongs to the reaction productionwhen dodecacarbonyltriiron reacted with substituted alkynes. This article leverages thereaction of dodecacarbonyltriiron and substituted alkyne. Not only get the substitutedcyclopentadiene compounds,but also extract five-membered ring containing Unsaturatedcarbon bonds. This article get two new compounds which has not been reported:Fc4C3(CO)2(5)and(η4-C4Ph2Fc2CO) Fe(CO)3(6). Their molecular structure were measuredby X-ray.Base on the above characteristic.The dissertation contains work as follows:1. Using fresh manganese dioxide oxidation style, with pentacarbonyl iron as rawmaterials, preparing dodecacarbonyltriiron. Ferrocenylacetylene was synthesized byelimination reaction of chloroacrolein and NaOH; Fc-C≡CCu was synthesized bysubstitution reaction of ferrocenylacetylene and CuI; Fc-I was synthesized by substitutionreaction of Fc-HgCl and I2; Fc-C≡C-Fc was was synthesized by coupled reaction ofFc-C≡CCu and Fc-I; Fc-C≡C-Ph was synthesized by coupled reaction of Fc-C≡CCu andPh-I.2. Compound1C4Ph4Fe2(CO)6(1) and2C4Ph4(CO)(2) were synthesized bycyclization reaction of Fe3(CO)12with diphenylacetypene using toluene as the solvent.3. Compound3C4H2Fc2Fe(CO)6(3) was synthesized by cyclization reaction ofFe3(CO)12with Ferrocenylacetylene using toluene as the solvent.4. Compound4C4Fc4(CO)Fe(CO)3(4) and5C3Fc4(CO)2(5) were synthesized bycyclization reaction of Fe3(CO)12with Fc-C≡C-Fc using toluene as the solvent. 5. Compound6η4-C4Ph2Fc2(CO) Fe(CO)3(6) was synthesized by cyclizationreaction of Fe3(CO)12with Fc-C≡C-Ph using toluene as the solvent.6. By infrared spectroscopy,research photochemical reactions of compound1in thesunshine and UV lamp,and extract compound2C4Ph4(CO)(2).7. At last,Compound1-6were characterized by IR,1H NMR,13C NMR、MS and X-raysingle crystal diffractometer.8. By Column chromatography and recrystallization technology, turned out singlecrystal compound1-6,and determined their crystal structure...
Keywords/Search Tags:Cyclopentadiene, Dodecacarbonyltriiron, Ferrocene, Diphenylacetylene, Synthesis and characterization
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