Acylphosphonamidates and α-hydroxyiminophosphonamidates. Synthesis of N-acylphosphordiamidates by Beckmann rearrangement. Crystal structure of (E)-α-hydroxyiminobenzyl-1-pyrrolidinylphosphinate

Eli Breuer*, Hisham Zaher, Zeev Tashma, Dan Gibson

*Corresponding author for this work

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Abstract

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 α-hydroxyiminobenzylphosphonamidates (5a-e), largely as (E)-isomers. The structure of methyl (E)-α-hydroxyimino-benzyl-1-pyrrolidinylphosphinate (5b) 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.

Original languageEnglish
Pages (from-to)515-520
Number of pages6
JournalHeteroatom Chemistry
Volume7
Issue number6
DOIs
StatePublished - 1996

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