Abstract
The reactivity of alkali metal ethoxides (EtOM, M = K, Na, and Li) toward phosphorus-centered electrophiles has been intensively investigated. The first study was performed by Buncel et al. for nucleophilic substitution reactions of 4-nitrophenyl diphenylphosphinate (1) with EtOM in anhydrous ethanol. They found that the plot of kobsd vs [EtOM] exhibits an upward curvature, while the reaction in the presence of a complexing agent (e.g., 18crown-6-ether or [2,2,2] cryptand for the reaction with EtO K) results in a linear plot. The reactivity has been reported to decrease in the order EtOLi > EtONa > EtOK > EtO. A similar result has been reported for alkaline ethanolysis of 4-nitrophenyl phenylphosphonate, 4-nitrophenyl diphenyl phosphate, 4-nitrophenyl methylphenylphosphinate, and 4-nitrophenyl dimethylphosphinate.
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