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Reaction of methyl benzoylphosphonochloridate (3) with a secondary or primary series of amines yielded methyl benzoylphosphonamidates, 4a-e. The latter compounds reacted with hydroxylamine to yield a-hydroxyiminobenzylphosphonamidates (Sa-e), largely as (E)-isomers. The structure of methyl (E)-a-hydroxyimino-benzyl-1 -pyrrolidinylphosphinate (Sb) was determined by single-crystal X-ray crystallography. Heating oximes 5a-e in boiling toluene caused them to undergo Beckmann rearrangement to N-benzoylphosphordiamidates 6a-e. 0 I996 John Wiley & Sons, Inc.
Acylphosphonates are versatile compounds, and their derivatives have recently been receiving increasing attention [ 11. In previous publications, we described results from our work on acylphospho-Dedicated to Prof. Louis D. Quin on the occasion of his retire-*To whom correspondence should be addressed. ?Affiliated with the David R. Bloom Center for Pharmacy. ment from the University of Massachusetts at Amherst.
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