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- On_water_reaction abstract "On water reactions are a group of organic reactions that take place as an emulsion in water and that exhibit an unusual reaction rate acceleration compared to the same reaction in an organic solvent or compared to the corresponding dry media reaction. This effect has been known for many years but in 2005 researchers in the group of K. Barry Sharpless presented a systematic study into this phenomenon.The rate acceleration is found in certain Claisen rearrangements. In one typical example of this reaction at room temperature the chemical yield was found to be 100% on water after 120 hours compared to 16% with the same reaction in toluene or 73% in the neat reaction.ClaesenrearrangementEnhanced reactivity is also found in cycloadditions. The reaction of quadricyclane with DEAD is a 2σ + 2σ + 2π cycloaddition that on water takes place within 10 minutes at room temperature with 82% yield. The same reaction in toluene takes 24 hours at 80°C with 70% yield. An emulsion reaction in fluorinated cyclohexane takes 36 hours and the neat reaction takes even longer (48 hours). QuadricyclaneOther reactions with apolar reactants such as Ene reactions and Diels-Alder reactions also exhibit rate accelerations. An explanation is not available but it involves hydrogen bonding and the presence of a small amount of dissolved solute. This reaction type is of interest to green chemistry because it greatly reduces the usage of organic solvents, reaction product isolation is relatively easy, and it increases the yields and chemical purity with little extra expenditure, if not less.".
- On_water_reaction thumbnail Claesenrearrangement.png?width=300.
- On_water_reaction wikiPageID "1939963".
- On_water_reaction wikiPageLength "5409".
- On_water_reaction wikiPageOutDegree "47".
- On_water_reaction wikiPageRevisionID "675634361".
- On_water_reaction wikiPageWikiLink 1,3-Dipolar_cycloaddition.
- On_water_reaction wikiPageWikiLink 1,3-dipolar_cycloaddition.
- On_water_reaction wikiPageWikiLink 1,3-dipole.
- On_water_reaction wikiPageWikiLink Acetonitrile.
- On_water_reaction wikiPageWikiLink Aldol_reaction.
- On_water_reaction wikiPageWikiLink Alkyne.
- On_water_reaction wikiPageWikiLink Allene.
- On_water_reaction wikiPageWikiLink Apolar.
- On_water_reaction wikiPageWikiLink Category:Organic_chemistry.
- On_water_reaction wikiPageWikiLink Chemical_yield.
- On_water_reaction wikiPageWikiLink Claisen_rearrangement.
- On_water_reaction wikiPageWikiLink Cycloaddition.
- On_water_reaction wikiPageWikiLink Cyclohexane.
- On_water_reaction wikiPageWikiLink Dichloromethane.
- On_water_reaction wikiPageWikiLink Diels-Alder_reaction.
- On_water_reaction wikiPageWikiLink Diels–Alder_reaction.
- On_water_reaction wikiPageWikiLink Diethyl_azodicarboxylate.
- On_water_reaction wikiPageWikiLink Dry_media_reaction.
- On_water_reaction wikiPageWikiLink Emulsion.
- On_water_reaction wikiPageWikiLink Enantiomer.
- On_water_reaction wikiPageWikiLink Enantioselectivity.
- On_water_reaction wikiPageWikiLink Ene_reaction.
- On_water_reaction wikiPageWikiLink Green_chemistry.
- On_water_reaction wikiPageWikiLink Hydrogen_bond.
- On_water_reaction wikiPageWikiLink Hydrogen_bonding.
- On_water_reaction wikiPageWikiLink Hydrophobe.
- On_water_reaction wikiPageWikiLink Indole.
- On_water_reaction wikiPageWikiLink Isoxazole.
- On_water_reaction wikiPageWikiLink K._Barry_Sharpless.
- On_water_reaction wikiPageWikiLink Karl_Barry_Sharpless.
- On_water_reaction wikiPageWikiLink Lithium_chloride.
- On_water_reaction wikiPageWikiLink Nitrone.
- On_water_reaction wikiPageWikiLink Organic_reaction.
- On_water_reaction wikiPageWikiLink Organic_solvent.
- On_water_reaction wikiPageWikiLink Organocatalysis.
- On_water_reaction wikiPageWikiLink Quadricyclane.
- On_water_reaction wikiPageWikiLink Quinone.
- On_water_reaction wikiPageWikiLink Reactant.
- On_water_reaction wikiPageWikiLink Reaction_rate.
- On_water_reaction wikiPageWikiLink Reagent.
- On_water_reaction wikiPageWikiLink Regioselective.
- On_water_reaction wikiPageWikiLink Regioselectivity.
- On_water_reaction wikiPageWikiLink Room_temperature.
- On_water_reaction wikiPageWikiLink Solvent.
- On_water_reaction wikiPageWikiLink Toluene.
- On_water_reaction wikiPageWikiLink Triphenylphosphine.
- On_water_reaction wikiPageWikiLink Yield_(chemistry).
- On_water_reaction wikiPageWikiLink Zwitterion.
- On_water_reaction wikiPageWikiLink File:Claesenrearrangement.png.
- On_water_reaction wikiPageWikiLink File:OnWaterQuinolineReaction.png.
- On_water_reaction wikiPageWikiLink File:OnWaterReactionApplication.png.
- On_water_reaction wikiPageWikiLink File:Quadricyclane2.gif.
- On_water_reaction wikiPageWikiLinkText "On water reaction".
- On_water_reaction wikiPageWikiLinkText "on water reaction".
- On_water_reaction wikiPageWikiLinkText "on water".
- On_water_reaction hasPhotoCollection On_water_reaction.
- On_water_reaction wikiPageUsesTemplate Template:Reflist.
- On_water_reaction subject Category:Organic_chemistry.
- On_water_reaction hypernym Group.
- On_water_reaction type Band.
- On_water_reaction comment "On water reactions are a group of organic reactions that take place as an emulsion in water and that exhibit an unusual reaction rate acceleration compared to the same reaction in an organic solvent or compared to the corresponding dry media reaction. This effect has been known for many years but in 2005 researchers in the group of K. Barry Sharpless presented a systematic study into this phenomenon.The rate acceleration is found in certain Claisen rearrangements.".
- On_water_reaction label "On water reaction".
- On_water_reaction sameAs m.067mzt.
- On_water_reaction sameAs Q7091637.
- On_water_reaction sameAs Q7091637.
- On_water_reaction wasDerivedFrom On_water_reaction?oldid=675634361.
- On_water_reaction depiction Claesenrearrangement.png.
- On_water_reaction isPrimaryTopicOf On_water_reaction.