Carbon Dioxide → 1-Methyl-1-oxo-1lambda5-phosphinane-4-carboxylic acid
Reaction equation
[CH3:1][P:2]1(=[O:14])[CH2:7][CH2:6][C:5](C(O)=O)([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.C(=O)=O>O>[CH3:1][P:2]1(=[O:14])[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 215 °C
Procedure
To a 50 mL microwave pressure flask equipped with a stir-bar was added 1-methyl-1-oxo-1λ5-phosphinane-4,4-dicarboxylic acid (0.25 g, 5.7 mmol) and water (20 mL) to give a suspension. The flask was sealed and heated to 215° C. over 60 seconds, at which point a pressure spike was observed. The flask was allowed to cool to room temperature then vented to release pressure from dissolved CO2. The resulting clear and colorless solution was concentrated by lyophilization to provide 1-methyl-1-oxo-1λ5-phosphinane-4-carboxylic acid in quantitative yield as a mixture of cis/trans isomers (˜2:1; identity of the favored isomer not determined). 1H NMR (400 MHz, D2O) δ ppm 2.6-2.4 (m, 1H), 2.2-1.6 (m, 8H), 1.48 (d, J=12.9 Hz, minor isomer, 1H), 1.44 (d, J=13.7 Hz, major isomer, 2H); ESMS m/z: found, 177 (M+1)+, 353 (2M+1)+.