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- Gilman_reagent abstract "A Gilman reagent is a lithium and copper (diorganocopper) reagent compound, R2CuLi, where R is an organic radical. These are useful because they react with organic chlorides, bromides, and iodides to replace the halide group with an R group. This is extremely useful in creating larger molecules from smaller ones.These reagents were discovered by Henry Gilman. Lithium dimethylcopper (CH3)2CuLi can be prepared by adding copper(I) iodide to methyllithium in tetrahydrofuran at −78 °C. In the reaction depicted below, the Gilman reagent is a methylating reagent reacting with an alkyne in a conjugate addition, and the negative charge is trapped in a nucleophilic acyl substitution with the ester group forming a cyclic enone.Gilman reagents have complicated structures in crystalline form and in solution. Lithium dimethylcuprate is a dimer in diethyl ether forming an 8-membered ring with two lithium atoms coordinating between two methyl groups. Similarly, lithium diphenylcuprate forms a dimeric etherate, [{Li(OEt2)}(CuPh2)]2, in the solid state.Lithium diphenylcuprate etherate dimer from crystal structure - 3D stick model Skeletal formula of lithium diphenylcuprate etherate dimerIf the Li+ ions are rendered inert by complexation with the crown ether 12-crown-4, the isolated diorganylcuprate anions that remain adopt a linear coordination geometry at copper.Dimethylcuprate anion from crystal structure Diphenylcuprate anion from crystal structure".
- Gilman_reagent thumbnail Gilman_reagent2.gif?width=300.
- Gilman_reagent wikiPageExternalLink 27.html.
- Gilman_reagent wikiPageID "455584".
- Gilman_reagent wikiPageLength "4248".
- Gilman_reagent wikiPageOutDegree "38".
- Gilman_reagent wikiPageRevisionID "646830642".
- Gilman_reagent wikiPageWikiLink 12-Crown-4.
- Gilman_reagent wikiPageWikiLink Alkyne.
- Gilman_reagent wikiPageWikiLink Bromide.
- Gilman_reagent wikiPageWikiLink Category:Lithium_compounds.
- Gilman_reagent wikiPageWikiLink Category:Organocopper_compounds.
- Gilman_reagent wikiPageWikiLink Category:Reagents_for_organic_chemistry.
- Gilman_reagent wikiPageWikiLink Chloride.
- Gilman_reagent wikiPageWikiLink Coordination_geometry.
- Gilman_reagent wikiPageWikiLink Copper.
- Gilman_reagent wikiPageWikiLink Copper(I)_iodide.
- Gilman_reagent wikiPageWikiLink Crown_ether.
- Gilman_reagent wikiPageWikiLink Diethyl_ether.
- Gilman_reagent wikiPageWikiLink Dimer_(chemistry).
- Gilman_reagent wikiPageWikiLink Enone.
- Gilman_reagent wikiPageWikiLink Ester.
- Gilman_reagent wikiPageWikiLink Grignard_reaction.
- Gilman_reagent wikiPageWikiLink Halide.
- Gilman_reagent wikiPageWikiLink Halocarbon.
- Gilman_reagent wikiPageWikiLink Henry_Gilman.
- Gilman_reagent wikiPageWikiLink Iodide.
- Gilman_reagent wikiPageWikiLink Lithium.
- Gilman_reagent wikiPageWikiLink Methyllithium.
- Gilman_reagent wikiPageWikiLink Molecule.
- Gilman_reagent wikiPageWikiLink Nucleophilic_acyl_substitution.
- Gilman_reagent wikiPageWikiLink Nucleophilic_conjugate_addition.
- Gilman_reagent wikiPageWikiLink Organocopper_compound.
- Gilman_reagent wikiPageWikiLink Organolithium_reagent.
- Gilman_reagent wikiPageWikiLink Radical_(chemistry).
- Gilman_reagent wikiPageWikiLink Reagent.
- Gilman_reagent wikiPageWikiLink Tetrahydrofuran.
- Gilman_reagent wikiPageWikiLink File:Dimethylcuprate-anion-from-xtal-3D-balls.png.
- Gilman_reagent wikiPageWikiLink File:Diphenylcuprate-anion-from-xtal-3D-balls.png.
- Gilman_reagent wikiPageWikiLink File:Gilman_reaction_example.png.
- Gilman_reagent wikiPageWikiLink File:Gilman_reagent2.gif.
- Gilman_reagent wikiPageWikiLink File:Gilman_reagent_+_RX.png.
- Gilman_reagent wikiPageWikiLink File:Lithium-diphenylcuprate-dietherate-dimer-from-xtal-3D-sticks-C.png.
- Gilman_reagent wikiPageWikiLink File:Lithium-diphenylcuprate-etherate-dimer-from-xtal-2D-skeletal.png.
- Gilman_reagent wikiPageWikiLinkText "Gilman reagent".
- Gilman_reagent wikiPageWikiLinkText "lithium dimethylcuprate".
- Gilman_reagent wikiPageUsesTemplate Template:Organometallics.
- Gilman_reagent wikiPageUsesTemplate Template:Reflist.
- Gilman_reagent subject Category:Lithium_compounds.
- Gilman_reagent subject Category:Organocopper_compounds.
- Gilman_reagent subject Category:Reagents_for_organic_chemistry.
- Gilman_reagent hypernym Lithium.
- Gilman_reagent type Reagent.
- Gilman_reagent type Redirect.
- Gilman_reagent comment "A Gilman reagent is a lithium and copper (diorganocopper) reagent compound, R2CuLi, where R is an organic radical. These are useful because they react with organic chlorides, bromides, and iodides to replace the halide group with an R group. This is extremely useful in creating larger molecules from smaller ones.These reagents were discovered by Henry Gilman. Lithium dimethylcopper (CH3)2CuLi can be prepared by adding copper(I) iodide to methyllithium in tetrahydrofuran at −78 °C.".
- Gilman_reagent label "Gilman reagent".
- Gilman_reagent sameAs Q516741.
- Gilman_reagent sameAs Gilman-Reagenz.
- Gilman_reagent sameAs Reactivo_de_Gilman.
- Gilman_reagent sameAs واکنشگر_گیلمان.
- Gilman_reagent sameAs Organocuprate_lithié.
- Gilman_reagent sameAs Reattivi_di_Gilman.
- Gilman_reagent sameAs ギルマン試薬.
- Gilman_reagent sameAs Gilman-reagens.
- Gilman_reagent sameAs Odczynnik_Gilmana.
- Gilman_reagent sameAs m.02bm5s.
- Gilman_reagent sameAs Q516741.
- Gilman_reagent sameAs 吉爾曼試劑.
- Gilman_reagent wasDerivedFrom Gilman_reagent?oldid=646830642.
- Gilman_reagent depiction Gilman_reagent2.gif.
- Gilman_reagent isPrimaryTopicOf Gilman_reagent.