, an electron-poor alkene that can serve as a dienophile. Conversion of a resulting secondary nitro group to a ketone can connect a Diels–Alder reaction to a Nef reaction.
A compound containing two carbon–carbon double bonds; conjugation is a separate structural qualification.
A five-carbon cyclic conjugated diene. Cycloaddition across its two double bonds produces a norbornene framework while retaining the original five-membered carbon ring.
Buta-1,3-diene is , a four-carbon diene with a conjugated system. Adjacent p orbitals allow electron delocalization across the two double bonds and the intervening single bond.
A suitable cisoid conformation can react with a dienophile in a Diels-Alder reaction. The need for the reactive conformation connects internal rotation with cycloaddition reactivity.
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Organic Chemistry by John McMurry. Chapter14, Conjugated Compounds: conjugated dienes and the Diels-Alder reaction
An alkene bearing two thioalkoxy groups on one carbon, . pi conjugation to a carbonyl can allow addition–elimination at that beta carbon with thiolate departure.
A puckered conformation with an approximately planar alkene end and a nonplanar saturated part. Bulky substituents commonly favor pseudoequatorial positions.
A terminal alkene has a carbon-carbon double bond at the end of its carbon framework, commonly written . The terminal carbon is a methylene group.
It differs from an internal alkene whose double-bond carbons both continue into carbon substituents. This distinction affects substitution, possible geometrical isomerism, and the regioselectivity of reactions across the double bond.
Addition polymerization consumes that double bond to form polystyrene while leaving phenyl groups as side substituents. This makes styrene a useful example of how a small molecular change, converting a pi bond into backbone sigma bonds, creates a macromolecular material.
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