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Intramolecular N-coordination in ketiminoboranes
Catherine E Bacon1, Liz Mansour, John J Hayward
1Department of Chemistry, The University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK.
Dalton Transactions (Cambridge, England : 2003)
|February 25, 2015
Summary
Researchers created novel bicyclic ketiminoboranes by reacting an imine with boron compounds. These compounds show basicity, reacting with acids, and their structures were determined.
Area of Science:
- Organometallic Chemistry
- Boron Chemistry
- Organic Synthesis
Background:
- Ketiminoboranes are versatile compounds with applications in synthesis.
- Understanding the reactivity and structural properties of ketiminoboranes is crucial for their further development.
Purpose of the Study:
- To synthesize novel bicyclic ketiminoboranes.
- To investigate the basicity and coordination behavior of these compounds.
- To determine the crystal structures of key derivatives.
Main Methods:
- Reaction of N-(trimethylsilyl)pyridine-2-carbaldimine with diethylmethoxyborane (Et2BOMe) or boron trifluoride etherate (BF3·Et2O).
- Characterization of the resulting bicyclic ketiminoboranes using spectroscopic techniques.
- X-ray crystallographic analysis of the hydrochloride (·HCl) and boron trifluoride etherate (·BF3) adducts, as well as a dipyridyl imine derivative hydrochloride (·HCl).
Main Results:
- Successful synthesis of bicyclic ketiminoboranes through intramolecular N-coordination.
- Demonstration of the basicity of the imine nitrogen atom.
- Elucidation of the structures of the ·HCl and ·BF3 adducts, confirming the proposed coordination modes.
Conclusions:
- The study successfully synthesized and characterized novel bicyclic ketiminoboranes.
- The findings highlight the Lewis basicity of the imine nitrogen and its ability to coordinate with Lewis acids.
- The reported structures provide valuable insights into the bonding and reactivity of these organoboron compounds.
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