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Fast tin-free hydrodehalogenation and reductive radical cyclization reactions: a new reduction process
Santiago E Vaillard1, Al Postigo, Roberto A Rossi
1INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, 5000 Córdoba, Argentina.
The Journal of Organic Chemistry
|April 3, 2004
Summary
Photostimulated reactions with ethyl benzoate monoanion yield reduced products efficiently. Aryl halides with double bonds form cyclized products, with yields improved by entrainment reagents.
Area of Science:
- Organic Chemistry
- Photochemistry
- Radical Reactions
Background:
- Photostimulated reactions offer unique pathways for chemical synthesis.
- Radical intermediates play a crucial role in many organic transformations.
Purpose of the Study:
- To investigate the photostimulated reactions of aryl and alkyl halides with ethyl benzoate monoanion.
- To explore the formation of cyclized reduced products from substrates with suitable double bonds.
Main Methods:
- Photostimulation of reactions involving aryl/alkyl chlorides and bromides with ethyl benzoate monoanion.
- Utilizing entrainment reagents like acetone enolate ion to enhance reaction yields.
- Competition experiments to determine relative reaction rates.
Main Results:
- High yields of reduced products were obtained from various aryl and alkyl halides.
- Cyclized reduced products were formed in high yields when aryl moieties contained double bonds.
- Specific examples include the synthesis of 3-methyl-2,3-dihydro-benzofuran with high yields, improved by entrainment reagents.
Conclusions:
- Ethyl benzoate monoanion is an effective reagent for photostimulated reduction of halides.
- The presence of double bonds in aryl moieties facilitates high-yield cyclization.
- Entrainment reagents can significantly improve yields in photostimulated reactions.