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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/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Reactions/Pericyclic_Reactions/Cope_RearrangementThe Cope rearrangement, not to be confused with the Cope elimination, is the conversion of a 1,5-diene to a more stable, constitutionally isomeric 1,5-diene at a very high temperature:
- https://chem.libretexts.org/Bookshelves/General_Chemistry/Book%3A_Structure_and_Reactivity_in_Organic_Biological_and_Inorganic_Chemistry_(Schaller)/V%3A__Reactivity_in_Organic_Biological_and_Inorganic_Chemistry_3/10%3A_Reactions_Under_Orbital_Control/10.02%3A_Cope_and_Claisen_RearrangementsA rearrangement is a reaction in which one molecule undergoes bonding changes, with the transfer of one atom or group from one position in the molecule to another. A proton is removed from one site an...A rearrangement is a reaction in which one molecule undergoes bonding changes, with the transfer of one atom or group from one position in the molecule to another. A proton is removed from one site and then a proton is placed on the new site. (In another variation, a proton is added at one site and then a proton is removed from the old site.) A Cope rearrangement can be considered to occur via a rearrangement of overlap between a group of orbitals around this ring.
- 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.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Basic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)/21%3A_Resonance_and_Molecular_Orbital_Methods/21.E%3A_Resonance_and_Molecular_Orbital_Methods_(Exercises)These are the homework exercises to accompany Chapter 21 of the Textmap for Basic Principles of Organic Chemistry (Roberts and Caserio).
- https://chem.libretexts.org/Ancillary_Materials/Reference/Organic_Chemistry_Glossary/Cope_RearrangementThe Cope rearrangement is the conversion of a 1,5-diene to a more stable, constitutionally isomeric 1,5-diene at a very high temperature.
