Diels-AlderRxn - Diels-Alder Reaction Otto Diels, Kurt...

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Diels-Alder Reaction Otto Diels, Kurt Alder; Nobel prize, 1950 Produces cyclohexene ring Diene + alkene or alkyne with electron- withdrawing group (dienophile) C C H H H W C C H H W H
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Examples of Diels-Alder Reactions H 3 C H 3 C N C C H C H H + H 3 C H 3 C C C H C N H H diene dienophile Diels-Alder adduct + O C OCH 3 C C C O OCH 3 C C O OCH 3 C OCH 3 O C
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Stereochemical Requirements Diene must be in s -cis conformation. Diene’s C1 and C4 p orbitals must overlap with dienophile’s p orbitals to form new sigma bonds. Both sigma bonds are on same face of the diene: syn stereochemistry.
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Concerted Mechanism (bond breaking and bond forming occurs all at once)
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Endo Rule The p orbitals of the electron-withdrawing groups on the dienophile have a secondary overlap with the p orbitals of C2 and C3 in the diene.
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Regiospecificity The 6-membered ring product of the Diels- Alder reaction will have electron-donating and electron-withdrawing groups 1,2 or 1,4 but not 1,3.
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Diels-AlderRxn - Diels-Alder Reaction Otto Diels, Kurt...

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