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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
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A new intermediate in the Prins reaction.

Shinichi Yamabe1, Takeshi Fukuda, Shoko Yamazaki

  • 1Fukui Institute for Fundamental Chemistry, Kyoto University Takano-Nishihiraki-cho 34-4, Sakyou-ku, Kyoto 606-8103, Japan.

Beilstein Journal of Organic Chemistry
|March 28, 2013
PubMed
Summary

This study explores Prins reactions using DFT calculations, revealing two distinct pathways. The research identifies key transition states and intermediates, offering insights into reaction mechanisms for alkene functionalization.

Keywords:
DFT calculationsPrins reactionhemiacetal intermediatehydrogen bondtransition state

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Reaction Mechanism Studies

Background:

  • The Prins reaction is a vital organic transformation for synthesizing valuable compounds.
  • Understanding the detailed mechanism of the Prins reaction is crucial for optimizing synthetic strategies.
  • Previous studies have explored various aspects, but detailed computational investigations of specific pathways remain valuable.

Purpose of the Study:

  • To elucidate the reaction pathways of the Prins reaction involving alkenes, formaldehyde, and hydronium ions.
  • To identify and characterize the transition states and intermediates involved in the reaction mechanism.
  • To compare the energetics and stability of different reaction channels.

Main Methods:

  • Density Functional Theory (DFT) calculations were employed to model the reaction.
  • Reaction paths were traced using a model system with varying alkene substituents (R = Me, Ph).
  • Classical trajectory dynamics calculations were performed on identified transition states.

Main Results:

  • A concerted pathway forming 1,3-diols was identified as the rate-determining step.
  • Two competing channels were observed: one leading to allylic alcohol and another forming a hemiacetal intermediate.
  • The hemiacetal intermediate was found to be in equilibrium with the 1,3-dioxane product, suggesting a reversible step.

Conclusions:

  • The study provides a detailed computational analysis of two Prins reaction pathways.
  • The findings highlight the formation of a novel hemiacetal intermediate and its equilibrium with the cyclic product.
  • The computational results offer valuable mechanistic insights for the Prins reaction and related transformations.