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- Smiles_rearrangement abstract "The Smiles rearrangement is an organic reaction and a rearrangement reaction. It is an intramolecular nucleophilic aromatic substitution of the type:where X in the arene compound can be a sulfone, a sulfide, an ether or any substituent capable of dislodging from the arene carrying a negative charge. The terminal functional group in the chain end Y is able to act as a strong nucleophile for instance an alcohol, amine or thiol.As in other nucleophilic aromatic substitutions the arene requires activation by an electron-withdrawing group preferably in the aromatic ortho position.In one modification called the Truce–Smiles rearrangement the incoming nucleophile is sufficiently strong that the arene does not require this additional activation, for example when the nucleophile is an organolithium. This reaction is exemplified by the conversion of an aryl sulfone into an sulfinic acid by action of n-butyllithium:This particular reaction requires the interaction of the alkyllithium group ortho to the sulfone group akin a directed ortho metalation.A conceptually related reaction is the Chapman rearrangement.A radical version of Smiles rearrangement is reported by Stephenson in 2015.The Hayashi rearrangement can be considered as the cationic counterpart of Smiles rearrangement.".
- Smiles_rearrangement thumbnail Smiles_rearrangement.png?width=300.
- Smiles_rearrangement wikiPageExternalLink V84P0325.pdf.
- Smiles_rearrangement wikiPageID "7552188".
- Smiles_rearrangement wikiPageLength "3139".
- Smiles_rearrangement wikiPageOutDegree "29".
- Smiles_rearrangement wikiPageRevisionID "705689657".
- Smiles_rearrangement wikiPageWikiLink Alcohol.
- Smiles_rearrangement wikiPageWikiLink Amide.
- Smiles_rearrangement wikiPageWikiLink Amine.
- Smiles_rearrangement wikiPageWikiLink Arene_substitution_pattern.
- Smiles_rearrangement wikiPageWikiLink Aromatic_hydrocarbon.
- Smiles_rearrangement wikiPageWikiLink Aryl.
- Smiles_rearrangement wikiPageWikiLink Category:Name_reactions.
- Smiles_rearrangement wikiPageWikiLink Category:Rearrangement_reactions.
- Smiles_rearrangement wikiPageWikiLink Directed_ortho_metalation.
- Smiles_rearrangement wikiPageWikiLink Ether.
- Smiles_rearrangement wikiPageWikiLink Hayashi_rearrangement.
- Smiles_rearrangement wikiPageWikiLink Intramolecular_reaction.
- Smiles_rearrangement wikiPageWikiLink N-Butyllithium.
- Smiles_rearrangement wikiPageWikiLink Nucleophile.
- Smiles_rearrangement wikiPageWikiLink Nucleophilic_aromatic_substitution.
- Smiles_rearrangement wikiPageWikiLink Organic_Syntheses.
- Smiles_rearrangement wikiPageWikiLink Organic_reaction.
- Smiles_rearrangement wikiPageWikiLink Organolithium_reagent.
- Smiles_rearrangement wikiPageWikiLink Polar_effect.
- Smiles_rearrangement wikiPageWikiLink Rearrangement_reaction.
- Smiles_rearrangement wikiPageWikiLink Substituent.
- Smiles_rearrangement wikiPageWikiLink Sulfide.
- Smiles_rearrangement wikiPageWikiLink Sulfinic_acid.
- Smiles_rearrangement wikiPageWikiLink Sulfone.
- Smiles_rearrangement wikiPageWikiLink Thiol.
- Smiles_rearrangement wikiPageWikiLink File:Smiles_rearrangement.png.
- Smiles_rearrangement wikiPageWikiLink File:Truce_Smiles_rearrangement.png.
- Smiles_rearrangement wikiPageWikiLinkText "Smiles rearrangement".
- Smiles_rearrangement subject Category:Name_reactions.
- Smiles_rearrangement subject Category:Rearrangement_reactions.
- Smiles_rearrangement hypernym Reaction.
- Smiles_rearrangement type Disease.
- Smiles_rearrangement type Eponym.
- Smiles_rearrangement type Reaction.
- Smiles_rearrangement comment "The Smiles rearrangement is an organic reaction and a rearrangement reaction. It is an intramolecular nucleophilic aromatic substitution of the type:where X in the arene compound can be a sulfone, a sulfide, an ether or any substituent capable of dislodging from the arene carrying a negative charge.".
- Smiles_rearrangement label "Smiles rearrangement".
- Smiles_rearrangement sameAs Q898710.
- Smiles_rearrangement sameAs Smiles-Umlagerung.
- Smiles_rearrangement sameAs Réarrangement_de_Smiles.
- Smiles_rearrangement sameAs スマイルス転位.
- Smiles_rearrangement sameAs Smiles-omlegging.
- Smiles_rearrangement sameAs m.026556n.
- Smiles_rearrangement sameAs Q898710.
- Smiles_rearrangement sameAs Smiles重排反应.
- Smiles_rearrangement wasDerivedFrom Smiles_rearrangement?oldid=705689657.
- Smiles_rearrangement depiction Smiles_rearrangement.png.
- Smiles_rearrangement isPrimaryTopicOf Smiles_rearrangement.