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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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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.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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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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Aromatic Hydrocarbon Cations: Structural Overview01:18

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Structures, Thermal Properties, and Reactivities of Cationic Rh-cod Complexes in Solid State (cod =

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Cationic rhodium complexes with 1,5-cyclooctadiene (cod) ligands exhibit disordered solid-state structures upon phase transitions. Structural disorder correlates with cation symmetry, influencing thermal stability and reactivity, particularly in hexafluoroantimonate salts.

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Area of Science:

  • Organometallic Chemistry
  • Solid-State Chemistry
  • Materials Science

Background:

  • Cationic rhodium complexes with 1,5-cyclooctadiene (cod) ligands are valuable precatalysts.
  • Their solid-state structures and thermal properties remain underexplored.
  • Understanding these properties is crucial for catalyst development.

Purpose of the Study:

  • To synthesize and characterize novel cationic rhodium(I)-diene complexes.
  • To investigate the impact of counteranions and ligands on their solid-state structures and phase behavior.
  • To explore the thermal stability and reactivity of these complexes.

Main Methods:

  • Synthesis of [Rh(cod)L]X complexes, where L = cod, benzene (C6H6), or toluene (PhMe), and X = SbF6, FSA, CF3BF3, or CB11H12.
  • X-ray crystallography to determine solid-state structures.
  • Differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) for thermal properties.
  • In situ single-crystal-to-single-crystal reactions to study ligand exchange.

Main Results:

  • Phase transitions lead to disordered solid-state structures in synthesized rhodium complexes.
  • Structural disorder increases with decreasing cation symmetry in SbF6 salts, with some exhibiting rotator phases or dynamic rotational disorder.
  • FSA salts show lower crystal symmetry and less cation disorder compared to SbF6 salts.
  • Arene-ligated FSA salts form anion-coordinated complexes upon melting.
  • Arene-ligated SbF6 salts undergo in situ ligand exchange to form [Rh(cod)L'2]SbF6.

Conclusions:

  • The counteranion significantly influences the solid-state structure and disorder of cationic rhodium complexes.
  • Phase transitions and structural disorder are key factors affecting the thermal stability and reactivity of these precatalysts.
  • The observed ligand-exchange reactions highlight the dynamic nature of these complexes in the solid state and upon melting.