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- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_III_(Morsch_et_al.)/29%3A_Orbitals_and_Organic_Chemistry_-_Pericyclic_Reactions/29.08%3A_Some_Examples_of_Sigmatropic_RearrangementsA sigmatropic rearrangement which involves a [1,5] hydrogen shift, like the one shown below illustrates, a hydrogen atom (s orbital) moving across a 5 atom system containing two conjugated double bond...A sigmatropic rearrangement which involves a [1,5] hydrogen shift, like the one shown below illustrates, a hydrogen atom (s orbital) moving across a 5 atom system containing two conjugated double bonds. The suprafacial nature of this reaction comes from the orbital symmetry of the HOMO from a 6 pi electron molecular orbital. During the reaction mechanism the hydrogen atom, an s orbital, is passes from one molecular to another of the same sign on the same side of the molecule or suprafacial.
- https://chem.libretexts.org/Courses/can/CHEM_232_-_Organic_Chemistry_II_(Puenzo)/15%3A_Orbitals_and_Organic_Chemistry_-_Pericyclic_Reactions/15.09%3A_Some_Examples_of_Sigmatropic_RearrangementsA sigmatropic rearrangement which involves a [1,5] hydrogen shift, like the one shown below illustrates, a hydrogen atom (s orbital) moving across a 5 atom system containing two conjugated double bond...A sigmatropic rearrangement which involves a [1,5] hydrogen shift, like the one shown below illustrates, a hydrogen atom (s orbital) moving across a 5 atom system containing two conjugated double bonds. The suprafacial nature of this reaction comes from the orbital symmetry of the HOMO from a 6 pi electron molecular orbital. During the reaction mechanism the hydrogen atom, an s orbital, is passes from one molecular to another of the same sign on the same side of the molecule or suprafacial.
- https://chem.libretexts.org/Workbench/LCDS_Organic_Chemistry_OER_Textbook_-_Todd_Trout/30%3A_Orbitals_and_Organic_Chemistry_-_Pericyclic_Reactions/30.09%3A_Some_Examples_of_Sigmatropic_RearrangementsTwo other important sigmatropic reactions are the Claisen rearrangement of either an allyl aryl ether ( H 2 C ═ CHCH 2 ─ O ─ Ar H 2 C ═ CHCH 2 ─ O ─ Ar ) or an allyl vinyl ( H 2 C ═ CHCH 2 ─ O ─ CH ═ ...Two other important sigmatropic reactions are the Claisen rearrangement of either an allyl aryl ether ( H 2 C ═ CHCH 2 ─ O ─ Ar H 2 C ═ CHCH 2 ─ O ─ Ar ) or an allyl vinyl ( H 2 C ═ CHCH 2 ─ O ─ CH ═ CH 2 H 2 C ═ CHCH 2 ─ O ─ CH ═ CH 2 ) ether, and the Cope rearrangement of a 1,5 hexadiene to an isomeric 1,5-diene.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/29%3A_Orbitals_and_Organic_Chemistry_-_Pericyclic_Reactions/29.08%3A_Some_Examples_of_Sigmatropic_RearrangementsA sigmatropic rearrangement which involves a [1,5] hydrogen shift, like the one shown below illustrates, a hydrogen atom (s orbital) moving across a 5 atom system containing two conjugated double bond...A sigmatropic rearrangement which involves a [1,5] hydrogen shift, like the one shown below illustrates, a hydrogen atom (s orbital) moving across a 5 atom system containing two conjugated double bonds. The suprafacial nature of this reaction comes from the orbital symmetry of the HOMO from a 6 pi electron molecular orbital. During the reaction mechanism the hydrogen atom, an s orbital, is passes from one molecular to another of the same sign on the same side of the molecule or suprafacial.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(OpenStax)/30%3A_Orbitals_and_Organic_Chemistry_-_Pericyclic_Reactions/30.08%3A_Some_Examples_of_Sigmatropic_RearrangementsThis section covers sigmatropic rearrangements, a type of pericyclic reaction where sigma bonds break and reform while the molecular structure rearranges. The examples illustrate the mechanisms and st...This section covers sigmatropic rearrangements, a type of pericyclic reaction where sigma bonds break and reform while the molecular structure rearranges. The examples illustrate the mechanisms and stereochemical outcomes of various rearrangements, such as the [3,3]-sigmatropic rearrangement. The discussion highlights the significance of orbital symmetry and how these reactions can occur in a concerted fashion.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Synthesis_(Shea)/01%3A_Pericyclic_Reactions/1.04%3A_Sigmatropic_RearrangementsThis chapter highlights synthetically useful sigmatropic rearrangements including hydride shifts, the Cope rearrangement, the Claisen rearrangement, and the Wittig rearrangement.
- https://chem.libretexts.org/Courses/can/CHEM_232_-_Organic_Chemistry_II_(Puenzo)/15%3A_Orbitals_and_Organic_Chemistry_-_Pericyclic_Reactions/15.08%3A_Sigmatropic_RearrangementsMolecular rearrangements in which a σ-bonded atom or group, flanked by one or more π-electron systems, shifts to a new location with a corresponding reorganization of the π-bonds are called sigmatropi...Molecular rearrangements in which a σ-bonded atom or group, flanked by one or more π-electron systems, shifts to a new location with a corresponding reorganization of the π-bonds are called sigmatropic reactions. The reactant and product have the same number and type of bonds, just different bond locations.
- https://chem.libretexts.org/Courses/University_of_Connecticut/Chem_2444%3A_(Second_Semester_Organic_Chemistry)_UConn/16%3A_Pericyclic_Reactions/16.06%3A_Sigmatropic_RearrangementsThese rearrangements are described by two numbers set in brackets, which refer to the relative distance (in atoms) each end of the σ-bond has moved, as illustrated by the first equation in the diagram...These rearrangements are described by two numbers set in brackets, which refer to the relative distance (in atoms) each end of the σ-bond has moved, as illustrated by the first equation in the diagram below. The [3,3] sigmatropic rearrangement of 1,5-dienes or allyl vinyl ethers, known respectively as the Cope and Claisen rearrangements, are among the most commonly used sigmatropic reactions.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_III_(Morsch_et_al.)/29%3A_Orbitals_and_Organic_Chemistry_-_Pericyclic_Reactions/29.07%3A_Sigmatropic_RearrangementsMolecular rearrangements in which a σ-bonded atom or group, flanked by one or more π-electron systems, shifts to a new location with a corresponding reorganization of the π-bonds are called sigmatropi...Molecular rearrangements in which a σ-bonded atom or group, flanked by one or more π-electron systems, shifts to a new location with a corresponding reorganization of the π-bonds are called sigmatropic reactions. The reactant and product have the same number and type of bonds, just different bond locations.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(OpenStax)/30%3A_Orbitals_and_Organic_Chemistry_-_Pericyclic_Reactions/30.07%3A_Sigmatropic_RearrangementsMolecular rearrangements in which a σ-bonded atom or group, flanked by one or more π-electron systems, shifts to a new location with a corresponding reorganization of the π-bonds are called sigmatropi...Molecular rearrangements in which a σ-bonded atom or group, flanked by one or more π-electron systems, shifts to a new location with a corresponding reorganization of the π-bonds are called sigmatropic reactions. The reactant and product have the same number and type of bonds, just different bond locations.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(Morsch_et_al.)/29%3A_Orbitals_and_Organic_Chemistry_-_Pericyclic_Reactions/29.08%3A_Some_Examples_of_Sigmatropic_RearrangementsA sigmatropic rearrangement which involves a [1,5] hydrogen shift, like the one shown below illustrates, a hydrogen atom (s orbital) moving across a 5 atom system containing two conjugated double bond...A sigmatropic rearrangement which involves a [1,5] hydrogen shift, like the one shown below illustrates, a hydrogen atom (s orbital) moving across a 5 atom system containing two conjugated double bonds. The suprafacial nature of this reaction comes from the orbital symmetry of the HOMO from a 6 pi electron molecular orbital. During the reaction mechanism the hydrogen atom, an s orbital, is passes from one molecular to another of the same sign on the same side of the molecule or suprafacial.
