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- Directed_ortho_metalation abstract "Directed ortho metalation (DoM) is an adaptation of electrophilic aromatic substitution in which electrophiles attach themselves exclusively to the ortho- position of a direct metalation group or DMG through the intermediary of an aryllithium compound. The DMG interacts with lithium through a hetero atom. Examples of DMG's are the methoxy group, a tertiary amine group and an amide group.The general principle is outlined in scheme 1. An aromatic ring system with a DMG group 1 interacts with an alkyllithium such as n-butyllithium in its specific aggregation state (hence (R-Li)n) to intermediate 2 since the hetero atom on the DMG is a Lewis base and lithium the Lewis acid. The very basic alkyllithium then deprotonates the ring in the nearest ortho- position forming the aryllithium 3 all the while maintaining the acid-base interaction. An electrophile reacts in the next phase in an electrophilic aromatic substitution with a strong preference for the lithium ipso position replacing the lithium atom.Ordinary electrophilic substitutions with an activating group show preference for both the ortho and para position, this reaction demonstrates increased regioselectivity because the ortho position alone is targeted. This reaction type was discovered independently by Henry Gilman and Georg Wittig around 1940.".
- Directed_ortho_metalation thumbnail Directedorthometalation.png?width=300.
- Directed_ortho_metalation wikiPageID "4686540".
- Directed_ortho_metalation wikiPageLength "7923".
- Directed_ortho_metalation wikiPageOutDegree "45".
- Directed_ortho_metalation wikiPageRevisionID "642595692".
- Directed_ortho_metalation wikiPageWikiLink 2,2,6,6-Tetramethylpiperidine.
- Directed_ortho_metalation wikiPageWikiLink Activating_group.
- Directed_ortho_metalation wikiPageWikiLink Alkyllithium.
- Directed_ortho_metalation wikiPageWikiLink Amide.
- Directed_ortho_metalation wikiPageWikiLink Amine.
- Directed_ortho_metalation wikiPageWikiLink Arene_substitution_pattern.
- Directed_ortho_metalation wikiPageWikiLink Aromatic_meta_substituent.
- Directed_ortho_metalation wikiPageWikiLink Asymmetric_induction.
- Directed_ortho_metalation wikiPageWikiLink Butyl.
- Directed_ortho_metalation wikiPageWikiLink Category:Substitution_reactions.
- Directed_ortho_metalation wikiPageWikiLink Deprotonation.
- Directed_ortho_metalation wikiPageWikiLink Di-tert-butylzinc.
- Directed_ortho_metalation wikiPageWikiLink Electrophile.
- Directed_ortho_metalation wikiPageWikiLink Electrophilic_aromatic_directing_groups.
- Directed_ortho_metalation wikiPageWikiLink Electrophilic_aromatic_substitution.
- Directed_ortho_metalation wikiPageWikiLink Enantiomer.
- Directed_ortho_metalation wikiPageWikiLink Enantiopure.
- Directed_ortho_metalation wikiPageWikiLink Georg_Wittig.
- Directed_ortho_metalation wikiPageWikiLink Henry_Gilman.
- Directed_ortho_metalation wikiPageWikiLink Hetero_atom.
- Directed_ortho_metalation wikiPageWikiLink Heteroatom.
- Directed_ortho_metalation wikiPageWikiLink Imine.
- Directed_ortho_metalation wikiPageWikiLink Iodine.
- Directed_ortho_metalation wikiPageWikiLink Ipso_substitution.
- Directed_ortho_metalation wikiPageWikiLink Lewis_acid.
- Directed_ortho_metalation wikiPageWikiLink Lewis_acids_and_bases.
- Directed_ortho_metalation wikiPageWikiLink Lewis_base.
- Directed_ortho_metalation wikiPageWikiLink Methoxy.
- Directed_ortho_metalation wikiPageWikiLink N-Butyllithium.
- Directed_ortho_metalation wikiPageWikiLink Nucleophile.
- Directed_ortho_metalation wikiPageWikiLink Nucleophilic_aromatic_substitution.
- Directed_ortho_metalation wikiPageWikiLink One-pot_synthesis.
- Directed_ortho_metalation wikiPageWikiLink Organolithium_reagent.
- Directed_ortho_metalation wikiPageWikiLink Ortho-.
- Directed_ortho_metalation wikiPageWikiLink Regioselectivity.
- Directed_ortho_metalation wikiPageWikiLink Sulfoxide.
- Directed_ortho_metalation wikiPageWikiLink Suzuki_reaction.
- Directed_ortho_metalation wikiPageWikiLink Tert-Butyllithium.
- Directed_ortho_metalation wikiPageWikiLink Tert-butyl.
- Directed_ortho_metalation wikiPageWikiLink Tertiary_amine.
- Directed_ortho_metalation wikiPageWikiLink Tetramethylethylenediamine.
- Directed_ortho_metalation wikiPageWikiLink Thiophenol.
- Directed_ortho_metalation wikiPageWikiLink Tosyl.
- Directed_ortho_metalation wikiPageWikiLink File:DOMapplication.png.
- Directed_ortho_metalation wikiPageWikiLink File:DOMapplicationII.png.
- Directed_ortho_metalation wikiPageWikiLink File:DOMsuzuki.png.
- Directed_ortho_metalation wikiPageWikiLink File:DirectedMetaMetallation.png.
- Directed_ortho_metalation wikiPageWikiLink File:Directedorthometalation.png.
- Directed_ortho_metalation wikiPageWikiLink File:DoM_Reactions.svg.
- Directed_ortho_metalation wikiPageWikiLink File:Victor_Snieckus_-_cropped.jpg.
- Directed_ortho_metalation wikiPageWikiLinkText "Directed ortho metalation".
- Directed_ortho_metalation wikiPageWikiLinkText "directed lithiation".
- Directed_ortho_metalation wikiPageWikiLinkText "directed ortho lithiation".
- Directed_ortho_metalation wikiPageWikiLinkText "directed ortho metalation".
- Directed_ortho_metalation wikiPageWikiLinkText "lithiation".
- Directed_ortho_metalation wikiPageWikiLinkText "ortho-metallation".
- Directed_ortho_metalation hasPhotoCollection Directed_ortho_metalation.
- Directed_ortho_metalation wikiPageUsesTemplate Template:Reflist.
- Directed_ortho_metalation subject Category:Substitution_reactions.
- Directed_ortho_metalation hypernym Adaptation.
- Directed_ortho_metalation type Film.
- Directed_ortho_metalation type Reaction.
- Directed_ortho_metalation comment "Directed ortho metalation (DoM) is an adaptation of electrophilic aromatic substitution in which electrophiles attach themselves exclusively to the ortho- position of a direct metalation group or DMG through the intermediary of an aryllithium compound. The DMG interacts with lithium through a hetero atom. Examples of DMG's are the methoxy group, a tertiary amine group and an amide group.The general principle is outlined in scheme 1.".
- Directed_ortho_metalation label "Directed ortho metalation".
- Directed_ortho_metalation sameAs Ortho-Metallierung.
- Directed_ortho_metalation sameAs Gestuurde_ortho-metallatie.
- Directed_ortho_metalation sameAs Orto-litowanie.
- Directed_ortho_metalation sameAs m.0chbh8.
- Directed_ortho_metalation sameAs Q900340.
- Directed_ortho_metalation sameAs Q900340.
- Directed_ortho_metalation sameAs 邻位定向金属化反应.
- Directed_ortho_metalation wasDerivedFrom Directed_ortho_metalation?oldid=642595692.
- Directed_ortho_metalation depiction Directedorthometalation.png.
- Directed_ortho_metalation isPrimaryTopicOf Directed_ortho_metalation.