| dbo:abstract |
In organic chemistry, an alkyne trimerisation is a [2+2+2] cycloaddition reaction in which three alkyne units (C≡C) react to form a benzene ring. The reaction requires a metal catalyst. The process is of historic interest as well as being applicable to organic synthesis. Being a cycloaddition reaction, it has high atom economy. Many variations have been developed, including cyclisation of mixtures of alkynes and alkenes as well as alkynes and nitriles. (en) Una reacción de trimerización de alquinos es una cicloadición [2+2+2] en la que tres alquinos reaccionan para formar un anillo de benceno. La reacción requiere un catalizador metálico. Este proceso es de interés histórico así como es aplicable a la síntesis orgánica. Al ser una reacción de cicloadición, tiene una alta economía atómica. Diversas variaciones han sido desarrolladas incluyendo la ciclación de mezclas de alquinos y alquenos así como alquinos y nitrilos. (es) Een alkyntrimerisatie is een chemische cyclisatiereactie, waarbij 3 alkynmoleculen reageren met elkaar om zo een benzeenverbinding te vormen. Het is echter een pseudo-pericyclische reactie, omdat de reactie nog nooit is waargenomen zonder het optreden van een metaal als katalysator. Een eenvoudig voorbeeld van alkyntrimerisatie is de vorming van 1,2,4- (97%) and 1,3,5-trifenylbenzeen (3%) uit drie moleculen fenylacetyleen. Hierbij treedt kobalt(II)bromide (CoBr2), zink (Zn), zinkchloride (ZnCl2) of acetonitril (CH3CN) op als katalysator: (nl) |
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wiki-commons:Special:FilePath/SimplifiedMechTrimeriz.png?width=300 |
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dbr:Catalyst dbr:Pyridine dbr:Electrophilic_aromatic_substitution dbr:Enyne dbr:Benzene dbr:Benzocyclobutene dbr:Bis(trimethylsilyl)acetylene dbr:Alkene dbr:Alkyne dbr:Arene_substitution_pattern dbr:Dötz_reaction dbc:Cycloadditions dbr:Complex_(chemistry) dbr:Nucleophilic_aromatic_substitution dbr:Organic_chemistry dbr:Aromaticity dbr:Benzyne dbr:Chirality_(chemistry) dbr:Steric_hindrance dbr:Organic_synthesis dbr:Strain_(chemistry) dbr:Trimethylsilyl dbr:Titanium_tetrachloride dbr:Triisobutylaluminium dbr:Walter_Reppe dbr:Wilkinson's_catalyst dbr:Cyclohexadiene dbr:Nitrile dbr:Cyclobutadiene dbr:Cyclooctatetraene dbr:Cyclopentadienylcobalt_dicarbonyl dbr:Nickel dbr:High_performance_liquid_chromatography dbr:Atom_economy dbr:Atropisomer dbc:Multiple_component_reactions dbc:Carbon-carbon_bond_forming_reactions dbr:Hexadehydro_Diels–Alder_reaction dbr:Molecular_tether dbr:Trimer_(chemistry) dbr:Transition_metal_alkyne_complex dbr:Aryne dbr:Phenylacetylene dbr:Diyne dbr:Regioselectivity dbr:Triflate dbr:Organocobalt_compound dbr:Helical_chirality dbr:Benzannulation dbr:Anthroquinone dbr:Cycloaddition_reaction dbr:File:1,7-Diyne_alkyne_cycloaddition.png dbr:File:2-Butyne_cyclotrimerization.png dbr:File:AlkyneTrimerizationInvolvingAnAryne.png dbr:File:Cyclotri_limits.png dbr:File:Cyclotri_other_methods.png dbr:File:Cyclotri_synth1.png dbr:File:Cyclotrimerisation_from_a_single_triyne.png dbr:File:SimplifiedMechTrimeriz.png dbr:File:TrimerizationInts.png |
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dbc:Cycloadditions dbc:Multiple_component_reactions dbc:Carbon-carbon_bond_forming_reactions |
| gold:hypernym |
dbr:Reaction |
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| rdfs:comment |
In organic chemistry, an alkyne trimerisation is a [2+2+2] cycloaddition reaction in which three alkyne units (C≡C) react to form a benzene ring. The reaction requires a metal catalyst. The process is of historic interest as well as being applicable to organic synthesis. Being a cycloaddition reaction, it has high atom economy. Many variations have been developed, including cyclisation of mixtures of alkynes and alkenes as well as alkynes and nitriles. (en) Una reacción de trimerización de alquinos es una cicloadición [2+2+2] en la que tres alquinos reaccionan para formar un anillo de benceno. La reacción requiere un catalizador metálico. Este proceso es de interés histórico así como es aplicable a la síntesis orgánica. Al ser una reacción de cicloadición, tiene una alta economía atómica. Diversas variaciones han sido desarrolladas incluyendo la ciclación de mezclas de alquinos y alquenos así como alquinos y nitrilos. (es) Een alkyntrimerisatie is een chemische cyclisatiereactie, waarbij 3 alkynmoleculen reageren met elkaar om zo een benzeenverbinding te vormen. Het is echter een pseudo-pericyclische reactie, omdat de reactie nog nooit is waargenomen zonder het optreden van een metaal als katalysator. Een eenvoudig voorbeeld van alkyntrimerisatie is de vorming van 1,2,4- (97%) and 1,3,5-trifenylbenzeen (3%) uit drie moleculen fenylacetyleen. Hierbij treedt kobalt(II)bromide (CoBr2), zink (Zn), zinkchloride (ZnCl2) of acetonitril (CH3CN) op als katalysator: (nl) |
| rdfs:label |
Alkyne trimerisation (en) Trimerización de alquinos (es) Alkyntrimerisatie (nl) |
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wikipedia-en:Alkyne_trimerisation?oldid=1111005310&ns=0 |
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wiki-commons:Special:FilePath/1,7-Diyne_alkyne_cycloaddition.png wiki-commons:Special:FilePath/2-Butyne_cyclotrimerization.png wiki-commons:Special:FilePath/AlkyneTrimerizationInvolvingAnAryne.png wiki-commons:Special:FilePath/Cyclotri_limits.png wiki-commons:Special:FilePath/Cyclotri_other_methods.png wiki-commons:Special:FilePath/Cyclotri_synth1.png wiki-commons:Special:FilePath/Cyclotrimerisation_from_a_single_triyne.png wiki-commons:Special:FilePath/SimplifiedMechTrimeriz.png wiki-commons:Special:FilePath/TrimerizationInts.png |
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