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- Simmons–Smith_reaction abstract "The Simmons–Smith reaction is an organic cheletropic reaction involving an organozinc carbenoid that reacts with an alkene (or alkyne) to form a cyclopropane. It is named after Howard Ensign Simmons, Jr. and Ronald D. Smith. It uses a methylene free radical intermediate that is delivered to both carbons of the alkene simultaneously, therefore the configuration of the double bond is preserved in the product and the reaction is stereospecific.Simmons–Smith reaction mechanismThus, cyclohexene, diiodomethane, and a zinc-copper couple (as iodomethylzinc iodide, ICH2ZnI) yield norcarane (bicyclo[4.1.0]heptane).An example of the Simmons–Smith reactionThe Simmons–Smith reaction is generally preferred over other methods of cyclopropanation, however it can be expensive due to the high cost of diiodomethane. Modifications involving cheaper alternatives have been developed, such as dibromomethane or diazomethane and zinc iodide. The reactivity of the system can also be increased by exchanging the zinc‑copper couple for diethylzinc, however as this reagent is pyrophoric it must be handled carefully.The Simmons–Smith reaction is generally subject to steric effects, and thus cyclopropanation usually takes place on the less hindered face. However, when a hydroxy substituent is present in the substrate in proximity to the double bond, the zinc coordinates with the hydroxy substituent, directing cyclopropanation cis to the hydroxyl group (which may not correspond to cyclopropanation of the sterically most accessible face of the double bond): An interactive 3D model of this reaction can be seen here (java required).An example of a stereoselective Simmons–Smith reactionThe Simmons–Smith reagent, namely diiodomethane and diethylzinc, can react with allylic thioethers to generate sulfur ylides, which can subsequently undergo a 2,3-sigmatropic rearrangement, and will not cyclopropanate an alkene in the same molecule unless excess Simmons–Smith reagent is used:An example of the use of the Simmons–Smith reagent to generate a sulfur ylide↑ ↑ ↑ ↑ ↑ ↑ ↑ ↑ ↑ ↑ ↑ ↑ ↑ ↑".
- Simmons–Smith_reaction thumbnail Simmons-Smith_carbene_addition.jpg?width=300.
- Simmons–Smith_reaction wikiPageExternalLink AsymCat_Simmons_Smith.html.
- Simmons–Smith_reaction wikiPageExternalLink Cyclopropanation.html.
- Simmons–Smith_reaction wikiPageExternalLink simmons-smith-reaction.shtm.
- Simmons–Smith_reaction wikiPageID "1693196".
- Simmons–Smith_reaction wikiPageLength "8984".
- Simmons–Smith_reaction wikiPageOutDegree "50".
- Simmons–Smith_reaction wikiPageRevisionID "688083605".
- Simmons–Smith_reaction wikiPageWikiLink 2,3-sigmatropic_rearrangement.
- Simmons–Smith_reaction wikiPageWikiLink Alkene.
- Simmons–Smith_reaction wikiPageWikiLink Alkyne.
- Simmons–Smith_reaction wikiPageWikiLink Allyl.
- Simmons–Smith_reaction wikiPageWikiLink Bisoxazoline_ligand.
- Simmons–Smith_reaction wikiPageWikiLink Carbenoid.
- Simmons–Smith_reaction wikiPageWikiLink Category:Addition_reactions.
- Simmons–Smith_reaction wikiPageWikiLink Category:Carbon-carbon_bond_forming_reactions.
- Simmons–Smith_reaction wikiPageWikiLink Category:Cheletropic_reactions.
- Simmons–Smith_reaction wikiPageWikiLink Category:Cyclopropanes.
- Simmons–Smith_reaction wikiPageWikiLink Category:Name_reactions.
- Simmons–Smith_reaction wikiPageWikiLink Cheletropic_reaction.
- Simmons–Smith_reaction wikiPageWikiLink Cinnamyl_alcohol.
- Simmons–Smith_reaction wikiPageWikiLink Cyclohexene.
- Simmons–Smith_reaction wikiPageWikiLink Cyclopropane.
- Simmons–Smith_reaction wikiPageWikiLink Diazo.
- Simmons–Smith_reaction wikiPageWikiLink Diazomethane.
- Simmons–Smith_reaction wikiPageWikiLink Dibromomethane.
- Simmons–Smith_reaction wikiPageWikiLink Dichloromethane.
- Simmons–Smith_reaction wikiPageWikiLink Diethylzinc.
- Simmons–Smith_reaction wikiPageWikiLink Diiodomethane.
- Simmons–Smith_reaction wikiPageWikiLink Diisobutylaluminium_hydride.
- Simmons–Smith_reaction wikiPageWikiLink Enantioselective_synthesis.
- Simmons–Smith_reaction wikiPageWikiLink Howard_Ensign_Simmons,_Jr..
- Simmons–Smith_reaction wikiPageWikiLink Hydroxyl.
- Simmons–Smith_reaction wikiPageWikiLink Iodomethylzinc_iodide.
- Simmons–Smith_reaction wikiPageWikiLink Lewis_acids_and_bases.
- Simmons–Smith_reaction wikiPageWikiLink Methylene_(compound).
- Simmons–Smith_reaction wikiPageWikiLink Norcarane.
- Simmons–Smith_reaction wikiPageWikiLink Organic_reaction.
- Simmons–Smith_reaction wikiPageWikiLink Organozinc_compound.
- Simmons–Smith_reaction wikiPageWikiLink Pyrophoricity.
- Simmons–Smith_reaction wikiPageWikiLink Radical_(chemistry).
- Simmons–Smith_reaction wikiPageWikiLink Salen_ligand.
- Simmons–Smith_reaction wikiPageWikiLink Steric_effects.
- Simmons–Smith_reaction wikiPageWikiLink Sulfonamide.
- Simmons–Smith_reaction wikiPageWikiLink Sulfur.
- Simmons–Smith_reaction wikiPageWikiLink Thioether.
- Simmons–Smith_reaction wikiPageWikiLink Ylide.
- Simmons–Smith_reaction wikiPageWikiLink Zinc-copper_couple.
- Simmons–Smith_reaction wikiPageWikiLink Zinc_iodide.
- Simmons–Smith_reaction wikiPageWikiLink File:AsymmSimmonsSmith2008.svg.
- Simmons–Smith_reaction wikiPageWikiLink File:AsymmetricSimmonsSmith.svg.
- Simmons–Smith_reaction wikiPageWikiLink File:Simmons-Smith_cyclohexene_to_bicyclo-4.1.0-heptane.svg.
- Simmons–Smith_reaction wikiPageWikiLink File:Simmons-Smith_reaction_mechanism.png.
- Simmons–Smith_reaction wikiPageWikiLink File:SimmonsSmithhydroxylEffect.svg.
- Simmons–Smith_reaction wikiPageWikiLink File:Simmons_smith_quaternary_carbon_rearrangement.svg.
- Simmons–Smith_reaction wikiPageWikiLinkText "Simmons–Smith reaction".
- Simmons–Smith_reaction wikiPageWikiLinkText "Simmons–Smith cyclopropanation".
- Simmons–Smith_reaction wikiPageWikiLinkText "Simmons–Smith reaction".
- Simmons–Smith_reaction caption "Simmons-Smith reaction in progress".
- Simmons–Smith_reaction name "Simmons-Smith reaction".
- Simmons–Smith_reaction namedafter Howard_Ensign_Simmons,_Jr..
- Simmons–Smith_reaction namedafter "Ronald D. Smith".
- Simmons–Smith_reaction type "Ring forming reaction".
- Simmons–Smith_reaction wikiPageUsesTemplate Template:Commonscat.
- Simmons–Smith_reaction wikiPageUsesTemplate Template:Infobox_industrial_process.
- Simmons–Smith_reaction wikiPageUsesTemplate Template:Reactionbox.
- Simmons–Smith_reaction wikiPageUsesTemplate Template:Reactionbox_Identifiers.
- Simmons–Smith_reaction wikiPageUsesTemplate Template:Reflist.
- Simmons–Smith_reaction subject Category:Addition_reactions.
- Simmons–Smith_reaction subject Category:Carbon-carbon_bond_forming_reactions.
- Simmons–Smith_reaction subject Category:Cheletropic_reactions.
- Simmons–Smith_reaction subject Category:Cyclopropanes.
- Simmons–Smith_reaction subject Category:Name_reactions.
- Simmons–Smith_reaction hypernym Reaction.
- Simmons–Smith_reaction type Disease.
- Simmons–Smith_reaction type Eponym.
- Simmons–Smith_reaction type Reaction.
- Simmons–Smith_reaction type Redirect.
- Simmons–Smith_reaction comment "The Simmons–Smith reaction is an organic cheletropic reaction involving an organozinc carbenoid that reacts with an alkene (or alkyne) to form a cyclopropane. It is named after Howard Ensign Simmons, Jr. and Ronald D. Smith.".
- Simmons–Smith_reaction label "Simmons–Smith reaction".
- Simmons–Smith_reaction sameAs Q903776.
- Simmons–Smith_reaction sameAs Reacció_de_Simmons-Smith.
- Simmons–Smith_reaction sameAs Category:Simmons-Smith_reaction.
- Simmons–Smith_reaction sameAs Simmons-Smith-Reaktion.
- Simmons–Smith_reaction sameAs Simmons–Smith-reaktio.
- Simmons–Smith_reaction sameAs Réaction_de_Simmons-Smith.
- Simmons–Smith_reaction sameAs Sintesi_di_Simmons-Smith.
- Simmons–Smith_reaction sameAs シモンズ・スミス反応.
- Simmons–Smith_reaction sameAs Simmons-Smith-reactie.
- Simmons–Smith_reaction sameAs Reação_de_Simmons-Smith.
- Simmons–Smith_reaction sameAs m.05nwvy.
- Simmons–Smith_reaction sameAs Реакция_Саймонса.
- Simmons–Smith_reaction sameAs Q903776.
- Simmons–Smith_reaction sameAs 西蒙斯–史密斯反应.
- Simmons–Smith_reaction wasDerivedFrom Simmons–Smith_reaction?oldid=688083605.
- Simmons–Smith_reaction depiction Simmons-Smith_carbene_addition.jpg.
- Simmons–Smith_reaction isPrimaryTopicOf Simmons–Smith_reaction.