A new nitrogen-to-oxygen phosphoryl migration

Article abstract of DOI:10.1080/10426509908037018

The reaction of diethyl N-acetyl-N-methylphosphoramidate 1 with aldehyde in the presence of LDA at -70°C results in the formation of the unstable oxyanion 6 which undergoes intramolecular rearrangement involving migration of a phosphoryl group from nitrogen to oxygen affording an amide anion 8. Subsequent proton transfer in 8 followed by elimination of phosphate anion provides the respective α,β-unsaturated N-methylcarboxamide 4. The formation of considerable amounts of diethyl N-methylphosphoramidate 5 is also always observed.

Full text of DOI:10.1080/10426509908037018

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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A NEW NITROGEN-TO-OXYGEN
PHOSPHORYL MIGRATION
A. Koziara a & A. Zwierzak a
a Institute of Organic Chemistry, Technical University
(Politechnika) , Zeromskiego 116, 90-924, Lodz,
Poland
Published online: 24 Sep 2006.
To cite this article: A. Koziara & A. Zwierzak (1999) A NEW NITROGEN-TO-OXYGEN
PHOSPHORYL MIGRATION, Phosphorus, Sulfur, and Silicon and the Related Elements,
149:1, 15-21, DOI: 10.1080/10426509908037018
To link to this article: http://dx.doi.org/10.1080/10426509908037018
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