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Abstract
A steric argument accounts for the orders of reactivity of two parallel series of hydrazines and hydroxylamines with p-nitrophenyl methylphosphonates. The α effect is not especially important. The unusually high reactivity of hydroxylamine may reflect O-attack for this species. In some cases hydrogen bonding to the phosphoryl oxygen atom in the transition state is a possibility. The results agree with prevailing theories on the forces which control nucleophilic substitution at a tetrahedral phosphorus atom.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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