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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
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Tetrahedral Complexes
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The cubyl cation rearrangements.

Said Jalife1, Sukanta Mondal1, Jose Luis Cabellos1

  • 1Departamento de Física Aplicada, Centro de Investigación y de Estudios Avanzados, Unidad Mérida. Km 6 Antigua Carretera a Progreso. Apdo. Postal 73, Cordemex, 97310, Mérida, Yuc., Mexico. gmerino@mda.cinvestav.mx mfernandez@mda.cinvestav.mx.

Chemical Communications (Cambridge, England)
|February 17, 2016
PubMed
Summary
This summary is machine-generated.

The cubyl cation can rearrange to the 7H(+)-pentalenyl cation, a process feasible in the gas phase. This rearrangement is kinetically stable at moderate temperatures but may occur at higher temperatures.

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Area of Science:

  • Computational Chemistry
  • Organic Chemistry
  • Physical Chemistry

Background:

  • The cubyl cation, a strained polycyclic hydrocarbon, presents unique structural and reactivity challenges.
  • Understanding the stability and rearrangement pathways of strained carbocations is crucial in organic chemistry.

Purpose of the Study:

  • To investigate the feasibility and mechanism of the cage-opening rearrangement of the cubyl cation to the 7H(+)-pentalenyl cation.
  • To determine the kinetic stability of the cubyl cation under various temperature conditions.

Main Methods:

  • Utilizing Born-Oppenheimer molecular dynamics simulations.
  • Performing high-level ab initio computations, including coupled cluster singles doubles with perturbative triples (CCSD(T)) and second-order Møller–Plesset perturbation theory (MP2) with def2-TZVP basis sets.

Main Results:

  • The rearrangement of the cubyl cation to the 7H(+)-pentalenyl cation is predicted to be feasible in the gas phase.
  • The rate-determining step involves the formation of the cuneyl cation, with a calculated activation barrier of 25.3 kcal mol(-1).
  • The cubyl cation exhibits kinetic stability at moderate temperatures but can undergo rearrangement at elevated temperatures.

Conclusions:

  • The cubyl cation is sufficiently kinetically stable for formation and trapping under moderate conditions.
  • Higher temperatures can facilitate the cage-opening rearrangement of the cubyl cation to the 7H(+)-pentalenyl cation.