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antarafacial and suprafacial wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 references toggle the table of contents antarafacial and suprafacial 6 languages čeština deutsch español polski português українська edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia redirected from suprafacial classification of pericyclic and electrocyclic chemical reactions in organic chemistry antarafacial woodward hoffmann symbol a and suprafacial s are two topological concepts describing the relationship between two simultaneous chemical bond making and or breaking processes in or around a reaction center 1 the reaction center can be a p or sp n orbital woodward hoffmann symbol ω a conjugated system π or even a sigma bond σ the relationship is antarafacial when opposite faces of the π system or isolated orbital are involved in the process think anti for a σ bond it corresponds to involvement of one interior lobe and one exterior lobe of the bond the relationship is suprafacial when the same face of the π system or isolated orbital are involved in the process think syn for a σ bond it corresponds to involvement of two interior lobes or two exterior lobes of the bond the components of all pericyclic reactions including sigmatropic reactions and cycloadditions and electrocyclizations can be classified as either suprafacial or antarafacial and this determines the stereochemistry in particular antarafacial topology corresponds to inversion of configuration for the carbon atom of a 1 n sigmatropic rearrangement and conrotation for electrocyclic ring closure while suprafacial corresponds to retention and disrotation an example is the 1 3 hydride shift in which the interacting frontier orbitals are the allyl free radical and the hydrogen 1s orbitals the suprafacial shift is symmetry forbidden because orbitals with opposite algebraic signs overlap the symmetry allowed antarafacial shift would require a strained transition state and is also unlikely in contrast a symmetry allowed and suprafacial 1 5 hydride shift is a common event 2 references edit iupac gold book definition link f a carey r j sundberg advanced organic chemistry part a isbn 0 306 41087 7 this stereochemistry article is a stub you can help wikipedia by adding missing information v t e retrieved from https en wikipedia org w index php title antarafacial_and_suprafacial oldid 1306615619 categories stereochemistry stereochemistry stubs hidden categories articles with short description short description matches wikidata all stub articles this page was last edited on 18 august 2025 at 19 21 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents antarafacial and suprafacial 6 languages add topic