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- Woodward–Hoffmann_rules abstract "The Woodward–Hoffmann rules, devised by Robert Burns Woodward and Roald Hoffmann, are a set of rules in organic chemistry predicting the barrier heights of pericyclic reactions based upon conservation of orbital symmetry. The Woodward–Hoffmann rules can be applied to understand electrocyclic reactions, cycloadditions (including cheletropic reactions), sigmatropic reactions, and group transfer reactions. Reactions are classified as allowed if the electronic barrier is low, and forbidden if the barrier is high. Forbidden reactions can still take place but require significantly more energy.The Woodward–Hoffmann rules were first formulated to explain the striking stereospecificity of electrocyclic reactions under thermal and photochemical control. Thermolysis of the substituted cyclobutene trans-1,2,3,4-tetramethylcyclobutene (1) gave only one geometric isomer, the (E,E)-3,4-dimethyl-2,4-hexadiene (2) as shown below; the (Z,Z) and the (E,Z) geometric isomers were not detected in the reaction. Similarly, thermolysis of cis-1,2,3,4-tetramethylcyclobutene (3) gave only the (E,Z) geometric isomer (4).Due to their elegance and simplicity, the Woodward–Hoffmann rules are credited with first exemplifying the power of molecular orbital theory to experimental chemists. Hoffmann was awarded the 1981 Nobel Prize in Chemistry for this work, shared with Kenichi Fukui who developed a similar model using frontier molecular orbital (FMO) theory; because Woodward had died two years before, he was not eligible to win what would have been his second Nobel Prize for Chemistry.".
- Woodward–Hoffmann_rules thumbnail Stereospecificity_electrocyclic_ring_opening1.png?width=300.
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- Woodward–Hoffmann_rules wikiPageLength "58556".
- Woodward–Hoffmann_rules wikiPageOutDegree "114".
- Woodward–Hoffmann_rules wikiPageRevisionID "705683551".
- Woodward–Hoffmann_rules wikiPageWikiLink Angewandte_Chemie.
- Woodward–Hoffmann_rules wikiPageWikiLink Antarafacial_and_suprafacial.
- Woodward–Hoffmann_rules wikiPageWikiLink Antiaromaticity.
- Woodward–Hoffmann_rules wikiPageWikiLink Aromaticity.
- Woodward–Hoffmann_rules wikiPageWikiLink Atomic_orbital.
- Woodward–Hoffmann_rules wikiPageWikiLink Avoided_crossing.
- Woodward–Hoffmann_rules wikiPageWikiLink Category:Cycloadditions.
- Woodward–Hoffmann_rules wikiPageWikiLink Category:Physical_organic_chemistry.
- Woodward–Hoffmann_rules wikiPageWikiLink Cheletropic_reaction.
- Woodward–Hoffmann_rules wikiPageWikiLink Claisen_rearrangement.
- Woodward–Hoffmann_rules wikiPageWikiLink Conjugated_system.
- Woodward–Hoffmann_rules wikiPageWikiLink Conrotatory_and_disrotatory.
- Woodward–Hoffmann_rules wikiPageWikiLink Cope_rearrangement.
- Woodward–Hoffmann_rules wikiPageWikiLink Cyclic_compound.
- Woodward–Hoffmann_rules wikiPageWikiLink Cycloaddition.
- Woodward–Hoffmann_rules wikiPageWikiLink Density_functional_theory.
- Woodward–Hoffmann_rules wikiPageWikiLink Diels–Alder_reaction.
- Woodward–Hoffmann_rules wikiPageWikiLink Electrocyclic_reaction.
- Woodward–Hoffmann_rules wikiPageWikiLink Elias_James_Corey.
- Woodward–Hoffmann_rules wikiPageWikiLink Excited_state.
- Woodward–Hoffmann_rules wikiPageWikiLink Frontier_molecular_orbital_theory.
- Woodward–Hoffmann_rules wikiPageWikiLink Ground_state.
- Woodward–Hoffmann_rules wikiPageWikiLink Group_transfer_reaction.
- Woodward–Hoffmann_rules wikiPageWikiLink LUMO.
- Woodward–Hoffmann_rules wikiPageWikiLink Journal_of_Organic_Chemistry.
- Woodward–Hoffmann_rules wikiPageWikiLink Kenichi_Fukui.
- Woodward–Hoffmann_rules wikiPageWikiLink Mechanistic_organic_photochemistry.
- Woodward–Hoffmann_rules wikiPageWikiLink Modular_arithmetic.
- Woodward–Hoffmann_rules wikiPageWikiLink Molecular_orbital_theory.
- Woodward–Hoffmann_rules wikiPageWikiLink Molecular_symmetry.
- Woodward–Hoffmann_rules wikiPageWikiLink Möbius–Hückel_concept.
- Woodward–Hoffmann_rules wikiPageWikiLink Nobel_Prize_in_Chemistry.
- Woodward–Hoffmann_rules wikiPageWikiLink Organic_chemistry.
- Woodward–Hoffmann_rules wikiPageWikiLink Pericyclic_reaction.
- Woodward–Hoffmann_rules wikiPageWikiLink Photochemistry.
- Woodward–Hoffmann_rules wikiPageWikiLink Polyene.
- Woodward–Hoffmann_rules wikiPageWikiLink Roald_Hoffmann.
- Woodward–Hoffmann_rules wikiPageWikiLink Robert_Burns_Woodward.
- Woodward–Hoffmann_rules wikiPageWikiLink Sigma_bond.
- Woodward–Hoffmann_rules wikiPageWikiLink Sigmatropic_reaction.
- Woodward–Hoffmann_rules wikiPageWikiLink Stereospecificity.
- Woodward–Hoffmann_rules wikiPageWikiLink Stress_(mechanics).
- Woodward–Hoffmann_rules wikiPageWikiLink Symmetry_element.
- Woodward–Hoffmann_rules wikiPageWikiLink Symmetry_operation.
- Woodward–Hoffmann_rules wikiPageWikiLink Thermal_decomposition.
- Woodward–Hoffmann_rules wikiPageWikiLink Thermal_energy.
- Woodward–Hoffmann_rules wikiPageWikiLink Torquoselectivity.
- Woodward–Hoffmann_rules wikiPageWikiLink Total_synthesis.
- Woodward–Hoffmann_rules wikiPageWikiLink Transition_state.
- Woodward–Hoffmann_rules wikiPageWikiLink Walsh_diagram.
- Woodward–Hoffmann_rules wikiPageWikiLink Woodwards_rules.
- Woodward–Hoffmann_rules wikiPageWikiLink File:2plus2_ret_stereochem.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:2plus2_symmelements.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:2splus2s_MO_correlation_diagram.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:2splus2s_statecorrdiag.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:4e_conrot_correlationdiagram.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:4e_conrot_statecorrelationdiagram.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:4e_disrot_correlationdiagram.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:4e_disrot_statecorrelationdiagram.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:4e_electrocyclic_mechstress_expmt.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:4e_electrocyclic_mechstress_versus_WH.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:Anti_WH_dimethylbicycloheptene.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:Butadiene_ES-2.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:CDFT_Diels_Alder.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:Conrot_disrot_v_supra_antara.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:CoreyElectrocyclicReaction1963.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:Diels_Alder_Symm.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:Diels_Alder_supra_supra.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:ES1_of_butadiene.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:Generalized_grouptransfer.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:Mobius_v_huckel_aromatic.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:Selection_rules_electrocyc_FMO.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:SigmatropicRearrangement_selection.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:Stereospecificity_electrocyclic_ring_opening1.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:Symm_MOs_cyclobutene.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:Symmetry_TransitionState.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:Symmetry_butadiene_MOs.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:Threethreesigmatropic_selection.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:WH_4n+2_thermal_MO.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:WH_4n_photo_MO.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:WH_4n_thermal_MO.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:WH_DielsAlder_MOCorrDiag.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:WH_DielsAlder_statecorrdiag.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:WH_grouptransfer.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:WH_grouptransfer_corrdiag.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:WH_symmetry_of_MOs_4e_cyclization.png.
- Woodward–Hoffmann_rules wikiPageWikiLink File:WH_symmetryelement_grouptransfer.png.
- Woodward–Hoffmann_rules wikiPageWikiLinkText "Woodward Hoffmann".
- Woodward–Hoffmann_rules wikiPageWikiLinkText "Woodward-Hoffmann".
- Woodward–Hoffmann_rules wikiPageWikiLinkText "Woodward–Hoffman".
- Woodward–Hoffmann_rules wikiPageWikiLinkText "Woodward–Hoffmann rules".
- Woodward–Hoffmann_rules wikiPageWikiLinkText "Woodward–Hoffmann selection rules".
- Woodward–Hoffmann_rules wikiPageWikiLinkText "Woodward–Hoffmann".
- Woodward–Hoffmann_rules wikiPageWikiLinkText "symmetry forbidden".