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Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
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Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
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Heterocycle synthesis based on allylic alcohol transposition using traceless trapping groups.

Youwei Xie1, Paul E Floreancig

  • 1Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 (USA).

Angewandte Chemie (International Ed. in English)
|April 9, 2014
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Summary

Allylic alcohols can be transformed into valuable oxygen-containing heterocycles using rhenium(VII) oxide (Re2 O7) catalyzed reactions. This method offers precise control over stereochemistry, enabling the synthesis of complex molecules.

Keywords:
allylic compoundscarbocationsdiastereoselectivityisomerizationoxygen heterocycles

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Allylic alcohols are versatile starting materials in organic synthesis.
  • Transposition reactions offer pathways to isomerize functional groups.
  • Controlling reaction pathways is crucial for selective synthesis.

Purpose of the Study:

  • To develop a versatile method for synthesizing oxygen-containing heterocycles.
  • To investigate the use of rhenium(VII) oxide (Re2 O7) in allylic alcohol transposition.
  • To achieve stereoselective synthesis of complex molecules.

Main Methods:

  • Utilizing Re2 O7 as a catalyst for allylic alcohol transposition.
  • Employing pendent electrophiles (aldehydes or ketones) to trap reaction intermediates.
  • Controlling reaction equilibrium by trapping specific isomers.
  • Employing bimolecular nucleophilic addition to terminate the reaction sequence.

Main Results:

  • Demonstrated a versatile method for synthesizing diverse oxygen-containing heterocycles.
  • Achieved formation of cyclic oxocarbenium ions through ionization.
  • Showcased control over multiple stereocenters with good to excellent selectivity.
  • Established a reaction sequence dictated by relative step rates.

Conclusions:

  • The developed Re2 O7-catalyzed transposition and trapping strategy is effective for heterocycle synthesis.
  • Understanding reaction kinetics allows for predictable stereochemical outcomes.
  • This methodology provides a powerful tool for constructing complex oxygen-containing molecules.