Woodward–Hoffmann rules

E309911

The Woodward–Hoffmann rules are fundamental principles in organic chemistry that predict the stereochemistry and feasibility of pericyclic reactions based on orbital symmetry considerations.

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Statements (48)

Predicate Object
instanceOf set of rules in organic chemistry ⓘ
theory in chemistry ⓘ
appliesTo 4n electron systems ⓘ
4n+2 electron systems ⓘ
cheletropic reactions ⓘ
cycloaddition reactions ⓘ
electrocyclic reactions ⓘ
group transfer reactions ⓘ
pericyclic reactions ⓘ
sigmatropic rearrangements ⓘ
assumes concerted reaction mechanism for pericyclic reactions ⓘ
basedOn molecular orbital theory ⓘ
orbital symmetry ⓘ
category reaction rules in chemistry ⓘ
criterion conservation of orbital symmetry ⓘ
correlation of reactant and product orbitals ⓘ
symmetry properties of frontier molecular orbitals ⓘ
determines allowedness of cycloadditions based on electron count ⓘ
stereospecificity of electrocyclic reactions ⓘ
developedBy Roald Hoffmann ⓘ
Robert Burns Woodward ⓘ
distinguishes thermal and photochemical pericyclic processes ⓘ
field organic chemistry ⓘ
physical organic chemistry ⓘ
theoretical chemistry ⓘ
influenced modern understanding of reaction mechanisms in organic chemistry ⓘ
language symmetry labels of molecular orbitals ⓘ
predicts allowed and forbidden pericyclic processes ⓘ
conrotatory versus disrotatory electrocyclic ring closures ⓘ
conrotatory versus disrotatory electrocyclic ring openings ⓘ
feasibility of pericyclic reactions ⓘ
stereochemistry of pericyclic reactions ⓘ
suprafacial versus antarafacial components in pericyclic reactions ⓘ
publicationYear 1965 ⓘ
recognizedBy Nobel Prize in Chemistry 1981 for Roald Hoffmann ⓘ
relatedTo Hückel molecular orbital theory ⓘ
correlation diagrams ⓘ
frontier molecular orbital theory ⓘ
pericyclic reaction mechanism ⓘ
status fundamental principles in organic chemistry ⓘ
usedIn analysis of concerted reaction pathways ⓘ
design of stereoselective organic syntheses ⓘ
usesConcept antarafacial interaction ⓘ
photochemical reactions ⓘ
suprafacial interaction ⓘ
symmetry-allowed reactions ⓘ
symmetry-forbidden reactions ⓘ
thermal reactions ⓘ

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Referenced by (9)

Full triples — surface form annotated when it differs from this entity's canonical label.

Robert Burns Woodward → notableWork → Woodward–Hoffmann rules ⓘ
Robert Burns Woodward → knownFor → Woodward–Hoffmann rules for pericyclic reactions ⓘ
linked to: Woodward–Hoffmann rules
Roald Hoffmann → knownFor → Woodward–Hoffmann rules ⓘ
Roald Hoffmann → hasWork → Woodward–Hoffmann rules ⓘ
R. B. Woodward → notableWork → Woodward–Hoffmann rules ⓘ
Roald Safran → notableWork → Woodward–Hoffmann rules ⓘ
Eschenmoser–Claisen rearrangement → governingRules → Woodward–Hoffmann rules for pericyclic reactions ⓘ
linked to: Woodward–Hoffmann rules
Diels–Alder reaction → obeys → Woodward–Hoffmann rules ⓘ