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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.
Selection Rules: Photochemical Activation
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Halogenation of Alkenes

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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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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Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
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Halogen Effect in Dual-Catalysis PhotoATRP.

Halil Ibrahim Coskun1, Rushik Radadiya1, Gorkem Yilmaz1

  • 1Chemistry Department, Carnegie Mellon University, Pittsburgh, Pennsylvania 15213, United States.

Macromolecules
|March 2, 2026
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Summary
This summary is machine-generated.

Bromine-based dual-catalyzed photoATRP offers faster polymerization and lower catalyst requirements than chlorine-based systems for methyl acrylate and methyl methacrylate. This study provides key insights for optimizing halogen and monomer choices in controlled radical polymerization.

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Area of Science:

  • Polymer Chemistry
  • Photocatalysis
  • Organic Synthesis

Background:

  • Atom Transfer Radical Polymerization (ATRP) is a powerful controlled radical polymerization technique.
  • Photoinduced ATRP (photoATRP) utilizes light to initiate and control polymerization, offering spatiotemporal control.
  • Dual-catalyzed photoATRP combines photocatalysis with a metal catalyst for enhanced control and efficiency.

Purpose of the Study:

  • To investigate the influence of halogen type (bromine vs. chlorine) on dual-catalyzed photoATRP of methyl acrylate (MA) and methyl methacrylate (MMA).
  • To compare the efficiency, kinetics, and control of Br-based versus Cl-based systems under green LED irradiation.
  • To establish design guidelines for optimizing halogen and monomer selection in photoATRP.

Main Methods:

  • Systematic investigation of photoATRP using rhodamine 6G (RD-6G) as a photocatalyst and CuX2/ligand complexes (X = Br, Cl) under green LED light.
  • Kinetic analysis of polymerization rates, activation, and deactivation processes.
  • Synthesis of polymers with defined chain ends (ω-bromo and ω-chloro) and characterization of dispersity.
  • Chain-extension experiments and temporal control studies to assess chain-end fidelity and light-mediated regulation.

Main Results:

  • Bromine-based systems demonstrated significantly faster activation and controlled polymerization compared to chlorine-based systems.
  • Lower catalyst and photocatalyst loadings were required for Br-based systems.
  • Polymerization of MA was faster than MMA, attributed to propagation rate constants and deactivator reduction rates.
  • Optimal ligand selection (Me6TREN for MA, TPMA for MMA) was crucial for controlling polymerization rate and achieving low dispersity.
  • High chain-end fidelity and efficient temporal control were confirmed.

Conclusions:

  • Halogen type plays a critical role in the performance of dual-catalyzed photoATRP.
  • Bromine-based systems offer superior performance in terms of speed and catalyst efficiency for MA and MMA polymerization.
  • The findings provide valuable design principles for tailoring photoATRP processes based on specific monomers and desired outcomes.