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Published on: January 3, 2018
Synthesis of phosphaformamidines and phosphaformamidinates
Maoying Song1, Bruno Donnadieu, Michele Soleilhavoup
1UCR-CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403, USA.
Chemistry, an Asian Journal
|June 7, 2007
Summary
Researchers developed a new synthetic route for phosphaformamidines and phosphaformamidinates, previously inaccessible compounds. This method offers efficient access to diverse derivatives, expanding synthetic capabilities in phosphorus chemistry.
Area of Science:
- Synthetic Organic Chemistry
- Organophosphorus Chemistry
Background:
- Phosphaamidines and phosphaamidinates are important classes of organophosphorus compounds.
- Previous synthetic methods had limitations in accessing a wide variety of these derivatives.
Purpose of the Study:
- To develop a novel, large-scale synthetic route to phosphaformamidines and phosphaformamidinates.
- To synthesize derivatives not previously accessible through known methods.
Main Methods:
- Reaction of thermally stable ethyl N-arylformimidates with lithium phosphanides.
- Utilized dialkyl-, diaryl-, and (aryl)(silyl)phosphanides.
- Addition of primary lithium arylphosphanides followed by n-butyllithium for phosphaformamidinates.
- Methanolysis for N-aryl-N-hydrogenophosphaformamidines.
Main Results:
- Successful synthesis of N-aryl phosphaformamidines in 60-80% yields.
- Obtained N-aryl-N-silylphosphaformamidine in 60% yield.
- Synthesized phosphaformamidinates in 70-88% yields.
- Produced N-aryl-N-hydrogenophosphaformamidines in 90-95% yields.
- Characterized the solid-state structure of a phosphaformamidinate.
Conclusions:
- A versatile and scalable synthetic strategy for phosphaformamidines and phosphaformamidinates has been established.
- The new route provides access to previously unavailable derivatives.
- The findings expand the synthetic toolkit for organophosphorus compounds.
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