Abstract
Reaction of dimethyl benzoylphosphonate with hydrazine hydrate gave exclusively benzhydrazide. Reaction of methyl lithium benzoylphosphonate with hydrazine hydrate gave the corresponding hydrazone (3) as a 65:35 mixture of E and Z isomers. Reaction of hydrazine hydrate with diisopropyl 4phthalimidobutanoylphosphonate gave mainly products resulting from nucleophilic attack of hydrazine on the carbonyl of the acylphosphonate and only a small percentage of phthalhydrazide. From our results it appears that the N-phthaloyl protecting group is not suitable for the transient protection of amino groups during attempts to synthesize aminoacylphosphonates.