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- Alkyne_zipper_reaction abstract "The alkyne zipper reaction is an organic reaction which isomerizes an organic compound containing an internal alkyne into a terminal alkyne. This was first reported by Charles Allen Brown and Ayako Yamashita in 1975. The isomerization reaction proceeds for straight-chain alkynes and acetylinic alcohols and provides a useful approach for remote functionalization in long-chain hydrocarbons.The reaction requires a strong base. The base used by Brown and Yamashita was potassium 1,3-diaminopropanide, generated in situ by adding potassium hydride to the solvent 1,3-diaminopropane. Alternative approaches have been investigated due to the expensive and hazardous nature of potassium hydride; ethylenediamine has been found to be an unsuitable replacement for 1,3-diaminopropane. As an example, for the synthesis of 9-decyn-1-ol from 2-decyn-1-ol, the lithium salt of 1,3-diaminopropane in the presence of potassium tert-butoxide affords yields of approximately 85%.HO–CH2C≡C–(CH2)6CH3 → HO(CH2)8–C≡CH↑ 1.0 1.1 ↑ 2.0 2.1".
- Alkyne_zipper_reaction wikiPageID "12217068".
- Alkyne_zipper_reaction wikiPageLength "1946".
- Alkyne_zipper_reaction wikiPageOutDegree "11".
- Alkyne_zipper_reaction wikiPageRevisionID "531658196".
- Alkyne_zipper_reaction wikiPageWikiLink 1,3-Diaminopropane.
- Alkyne_zipper_reaction wikiPageWikiLink 1,3-diaminopropanide.
- Alkyne_zipper_reaction wikiPageWikiLink Alkyne.
- Alkyne_zipper_reaction wikiPageWikiLink Base_(chemistry).
- Alkyne_zipper_reaction wikiPageWikiLink Category:Rearrangement_reactions.
- Alkyne_zipper_reaction wikiPageWikiLink Ethylenediamine.
- Alkyne_zipper_reaction wikiPageWikiLink Isomerization.
- Alkyne_zipper_reaction wikiPageWikiLink Organic_reaction.
- Alkyne_zipper_reaction wikiPageWikiLink Potassium_hydride.
- Alkyne_zipper_reaction wikiPageWikiLink Potassium_tert-butoxide.
- Alkyne_zipper_reaction wikiPageWikiLink Solvent.
- Alkyne_zipper_reaction wikiPageWikiLinkText "Alkyne zipper reaction".
- Alkyne_zipper_reaction wikiPageWikiLinkText "alkyne zipper reaction".
- Alkyne_zipper_reaction subject Category:Rearrangement_reactions.
- Alkyne_zipper_reaction hypernym Reaction.
- Alkyne_zipper_reaction type Disease.
- Alkyne_zipper_reaction type Reaction.
- Alkyne_zipper_reaction comment "The alkyne zipper reaction is an organic reaction which isomerizes an organic compound containing an internal alkyne into a terminal alkyne. This was first reported by Charles Allen Brown and Ayako Yamashita in 1975. The isomerization reaction proceeds for straight-chain alkynes and acetylinic alcohols and provides a useful approach for remote functionalization in long-chain hydrocarbons.The reaction requires a strong base.".
- Alkyne_zipper_reaction label "Alkyne zipper reaction".
- Alkyne_zipper_reaction sameAs Q4727745.
- Alkyne_zipper_reaction sameAs m.02vw6ln.
- Alkyne_zipper_reaction sameAs Q4727745.
- Alkyne_zipper_reaction wasDerivedFrom Alkyne_zipper_reaction?oldid=531658196.
- Alkyne_zipper_reaction isPrimaryTopicOf Alkyne_zipper_reaction.