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- Danishefsky's_diene abstract "Danishefsky’s diene (Kitahara diene) is an organosilicon compound and a diene with the formal name trans-1-methoxy-3-trimethylsilyloxy-1,3-butadiene named after Samuel J. Danishefsky. Because the diene is very electron-rich it is a very reactive reagent in Diels-Alder reactions. This diene reacts rapidly with electrophilic alkenes, such as maleic anhydride.The OMe group promotes highly regioselective additions.It was first synthesized by the reaction of trimethylsilyl chloride with 4-methoxy-3-buten-2-one and zinc chloride:The diene has two features of interest: the substituents promote regiospecific addition to unsymmetrical dienophiles and the resulting adduct is amenable to further functional group manipulations after the addition reaction. High regioselectivity is obtained with unsymmetrical alkenes with a preference for a 1,2-relation of the ether group with the electron-deficient alkene-carbon. All this is exemplified in this Aza Diels-Alder reaction:In the cycloaddition product, the silyl ether is a synthon for a carbonyl group via the enol. The methoxy group is susceptible to an elimination reaction enabling the formation of a new alkene group.".
- Danishefsky's_diene thumbnail Danishefsky-Diene_Structural_Formulae.png?width=300.
- Danishefsky's_diene wikiPageID "7067238".
- Danishefsky's_diene wikiPageRevisionID "601702933".
- Danishefsky's_diene hasPhotoCollection Danishefsky's_diene.
- Danishefsky's_diene imagefile "Danishefsky-Diene Structural Formulae.png".
- Danishefsky's_diene imagename "Structural formula of".
- Danishefsky's_diene imagesize "150".
- Danishefsky's_diene othernames "-1".
- Danishefsky's_diene othernames "Kitahara diene".
- Danishefsky's_diene othernames "trans-1-Methoxy-3-trimethylsilyloxy-1,3-butadiene".
- Danishefsky's_diene verifiedrevid "401977521".
- Danishefsky's_diene watchedfields "changed".
- Danishefsky's_diene subject Category:Dienes.
- Danishefsky's_diene subject Category:Reagents_for_organic_chemistry.
- Danishefsky's_diene subject Category:Silanes.
- Danishefsky's_diene type Agent114778436.
- Danishefsky's_diene type CausalAgent100007347.
- Danishefsky's_diene type ChemicalAgent114779550.
- Danishefsky's_diene type Matter100020827.
- Danishefsky's_diene type PhysicalEntity100001930.
- Danishefsky's_diene type Reagent114778982.
- Danishefsky's_diene type ReagentsForOrganicChemistry.
- Danishefsky's_diene type Substance100020090.
- Danishefsky's_diene type ChemicalCompound.
- Danishefsky's_diene type ChemicalSubstance.
- Danishefsky's_diene type ChemicalObject.
- Danishefsky's_diene type Thing.
- Danishefsky's_diene comment "Danishefsky’s diene (Kitahara diene) is an organosilicon compound and a diene with the formal name trans-1-methoxy-3-trimethylsilyloxy-1,3-butadiene named after Samuel J. Danishefsky. Because the diene is very electron-rich it is a very reactive reagent in Diels-Alder reactions.".
- Danishefsky's_diene label "Danishefsky's diene".
- Danishefsky's_diene label "Danishefsky-Dien".
- Danishefsky's_diene label "ダニシェフスキージエン".
- Danishefsky's_diene sameAs Danishefsky-Dien.
- Danishefsky's_diene sameAs ダニシェフスキージエン.
- Danishefsky's_diene sameAs m.0h2p_5.
- Danishefsky's_diene sameAs Q904983.
- Danishefsky's_diene sameAs Q904983.
- Danishefsky's_diene sameAs Danishefsky's_diene.
- Danishefsky's_diene wasDerivedFrom Danishefsky's_diene?oldid=601702933.
- Danishefsky's_diene depiction Danishefsky-Diene_Structural_Formulae.png.
- Danishefsky's_diene isPrimaryTopicOf Danishefsky's_diene.
