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Intramolecular hydrogen-bond participation in phosphonylammonium salt formation
A B Smith1, L Ducry, R M Corbett
1Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Organic Letters
|December 2, 2000
Summary
Researchers investigated phosphonochloridates and phosphonyl dichlorides reactivity. Intramolecular hydrogen bonding is crucial for phosphonylammonium salt formation, making phosphorus more electron-deficient.
Area of Science:
- Organic Chemistry
- Organophosphorus Chemistry
Background:
- Phosphonochloridates and phosphonyl dichlorides are reactive organophosphorus compounds.
- Understanding their reactivity is key to developing new synthetic methodologies.
Purpose of the Study:
- To investigate the reactivity of phosphonochloridates and phosphonyl dichlorides with triethylamine.
- To elucidate the role of intramolecular hydrogen bonding in phosphonylammonium salt formation.
Main Methods:
- Synthesis of various phosphonochloridates and phosphonyl dichlorides.
- Reactivity studies using phosphorus-31 Nuclear Magnetic Resonance ((31)P NMR) spectroscopy.
- Analysis of reaction products and intermediates.
Main Results:
- The preparation of a series of phosphonochloridates and phosphonyl dichlorides was successful.
- (31)P NMR spectroscopy revealed distinct reactivity patterns with triethylamine.
- Evidence was found for the requirement of an intramolecular hydrogen bond in phosphonylammonium salt formation.
Conclusions:
- Intramolecular hydrogen bonding plays a critical role in stabilizing the transition state for phosphonylammonium salt formation.
- This hydrogen bonding renders the phosphorus atom more electron-deficient, facilitating nucleophilic attack.
- The findings provide valuable insights into the reaction mechanisms of organophosphorus compounds.