The rates of alkaline hydrolysis and reaction with n-butylamine of a series of phosphorylating agents of general formula (PriO)2POX, [X = F, Cl, CN, and (PriO)2P:O] are measured. The different rate orders are explained in terms of the relative leaving-group tendencies of X, H2O, and BuNH2 in transient penta-covalent intermediates. The general-base catalysis of the hydrolysis of the fluoridate by n-butylamine is discussed.
R. F. Hudson and R. Greenhalgh, J. Chem. Soc. B, 1969, 325 DOI: 10.1039/J29690000325
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