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Oxaphosphirane-borane complexes: ring strain and migratory insertion/ring-opening reactions.

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This study uses DFT calculations to show that oxaphosphiranes preferentially bond with boranes at phosphorus over oxygen. Stronger P-B bonds lead to ring strain release and unique ring-opening reactions.

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Area of Science:

  • Organophosphorus Chemistry
  • Computational Chemistry
  • Borane Chemistry

Background:

  • Oxaphosphiranes are strained heterocyclic compounds with potential reactivity.
  • Understanding their interaction with Lewis acids like boranes is crucial for synthetic applications.

Purpose of the Study:

  • To predict and analyze the complexation behavior of oxaphosphiranes with various borane reagents.
  • To investigate the factors governing P- versus O-complexation and subsequent reactivity.

Main Methods:

  • Density Functional Theory (DFT) calculations were employed.
  • HSAB (Hard and Soft Acids and Bases) principles were used to rationalize bonding preferences.
  • Analysis of bond strengths, dissociation energies, ring strain, and charge transfer was performed.

Main Results:

  • DFT-based HSAB parameters accurately predict preferential P-complexation of oxaphosphiranes with boranes.
  • Strong P-B bonds were observed for specific borane substituents (H, Cl, C6F5), correlating with high dissociation energies.
  • P-complexation significantly increased ring strain, while O-complexation moderately decreased it.
  • Increased charge transfer from oxaphosphirane to borane weakened B-R bonds, facilitating migratory insertion and ring-opening reactions.

Conclusions:

  • Oxaphosphiranes exhibit a preference for P-complexation with boranes, driven by HSAB principles and leading to strong P-B bonds.
  • The observed increase in ring strain upon P-complexation is a key driving force for subsequent ring-opening reactions.
  • This study provides insights into the reactivity patterns of oxaphosphiranes with borane Lewis acids.