2628-93-5Relevant academic research and scientific papers
Stereoselectivity in Fragmentation and Rearrangement of α-Hydroxyiminophosphinates and -phosphonates. A Synthetic Approach to Acylphosphon- and phosphor-amidates. Crystal Structures of Methyl (E)-α-Hydroxyiminobenzylphenylphosphinate and Methyl Benzoylphenylphosphonamidate
Breuer, Eli,Schlossman, Ada,Safadi, Muhammad,Gibson, Dan,Chorev, Michael,Leader, Haim
, p. 3263 - 3269 (2007/10/02)
Reaction of methyl benzoylphenylphosphinate 1 with hydroxylamine gave methyl α-hydroxyiminobenzylphenylphosphinate 2 as a mixture of E and Z isomers with the E isomer predominating.Pure (E)-2 when heated gave methyl N-benzoylphenylphosphonamidate 3 as the sole product.In contrast, (Z)-2 when heated gave, as a result of fragmentation, mainly methyl hydrogen phenylphosphonate 4 and benzonitrile, together with methyl N-phenylcarbamoylphenylphosphinate 5 as the minor product; the latter results from Beckmann rearrangement of (Z)-2.Analogous behaviour is exhibited by the two geometrical isomers of dimethyl α-hydroxyiminobenzylphenylphosphinate (E)-2 and methyl benzoylphenylphosphonamidate 3 are reported.
