WebStereochemical Notations. William Reusch. Michigan State University. Molecular rearrangements in which a σ-bonded atom or group, flanked by one or more π-electron … A sigmatropic reaction in organic chemistry is a pericyclic reaction wherein the net result is one σ-bond is changed to another σ-bond in an uncatalyzed intramolecular reaction. The name sigmatropic is the result of a compounding of the long-established sigma designation from single carbon–carbon bonds … See more Woodward–Hoffman sigmatropic shift nomenclature Sigmatropic rearrangements are concisely described by an order term [i,j], which is defined as the migration of a σ-bond adjacent to one or … See more [1,3] shifts Thermal hydride shifts In a thermal [1,3] hydride shift, a hydride moves three atoms. The Woodward–Hoffmann rules dictate that it would proceed in an antarafacial shift. Although such a … See more • 2,3-sigmatropic rearrangement • NIH shift • Frontier molecular orbital theory See more
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