TY - JOUR
T1 - Acylphosphonamidates and α-hydroxyiminophosphonamidates. Synthesis of N-acylphosphordiamidates by Beckmann rearrangement. Crystal structure of (E)-α-hydroxyiminobenzyl-1-pyrrolidinylphosphinate
AU - Breuer, Eli
AU - Zaher, Hisham
AU - Tashma, Zeev
AU - Gibson, Dan
PY - 1996
Y1 - 1996
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0010785013&partnerID=8YFLogxK
U2 - 10.1002/(SICI)1098-1071(199611)7:6<515::AID-HC13>3.0.CO;2-T
DO - 10.1002/(SICI)1098-1071(199611)7:6<515::AID-HC13>3.0.CO;2-T
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AN - SCOPUS:0010785013
SN - 1042-7163
VL - 7
SP - 515
EP - 520
JO - Heteroatom Chemistry
JF - Heteroatom Chemistry
IS - 6
ER -