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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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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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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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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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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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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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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Enantioselective Magneto-Chiral Photochemistry Rediscovered.

Maria Sara Raju1, Maxime Aragon-Alberti1, Kevin Cardenas1

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Magneto-chiral photochemistry (MChPh) can induce enantiomeric excess (ee) in molecules. This study reexplores MChPh, achieving a 0.50% ee, surpassing circularly polarized photochemistry.

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Area of Science:

  • Photochemistry
  • Chirality
  • Magneto-optics

Background:

  • Enantioselective magneto-chiral photochemistry (MChPh) was first demonstrated 25 years ago but has not been re-explored.
  • MChPh's potential role in the origin of molecular homochirality remains significant.
  • No quantitative studies on MChPh's enantiomeric excess (ee) as a function of magnetic field and wavelength exist.

Purpose of the Study:

  • To re-evaluate enantioselective photochemical reactivity using MChPh.
  • To quantitatively determine the achievable enantiomeric excess (ee) via MChPh.
  • To compare MChPh with circularly polarized photochemistry (CPPh) for enantioselectivity.

Main Methods:

  • Magneto-chiral dichroism (MChD) studies were performed.
  • MChPh experiments were conducted on potassium tris-(oxalato)-chromate-(III).
  • Racemic mixtures were irradiated under specific magnetic fields and wavelengths.

Main Results:

  • An enantiomeric excess (ee) of 0.50% was achieved using MChPh.
  • The experiment utilized irradiation at λ = 695.5 nm with 500 mW power.
  • A magnetic field of 30 T was applied for 30 minutes at 5 °C.
  • MChPh yielded a higher ee compared to CPPh under identical conditions.

Conclusions:

  • MChPh is a viable method for inducing enantioselectivity in photochemical reactions.
  • The study provides quantitative data on MChPh's effectiveness.
  • MChPh demonstrates potential superiority over CPPh in generating enantiomeric excess.