Accession Number : AD0616800

Title :   THE PHOSPHORYLATION OF 2-METHYL-DELTA(2)OXAZOLINE,

Corporate Author : DEFENCE CHEMICAL BIOLOGICAL AND RADIATION LABS OTTAWA (ONTARIO)

Personal Author(s) : Greenhalgh,R.

Report Date : 05 JAN 1962

Pagination or Media Count : 8

Abstract : In common with other acylating agents, diisopropyl phosphorochloridate reacts with 2-methyl-delta(2)oxazoline in aqueous and ethereal media to yield Nphosphoryl derivatives. In both media, phosphorylation is followed by ring opening between positions 1 and 5, as shown by the isolation of diisopropyl N-acetyl-N-2chloroethylphosphoramidate and diisopropyl N-acetyl-N2-hydroxyethylphosphoramidate. The latter compound undergoes further rearrangement, being slowly converted to diisopropyl N-2-acetoxyethylphosphoramidate in aqueous bicarbonate solution. Nuclear magnetic resonance studies of 2-methyl-delta(2)-oxazoline in aqueous bicarbonate solution (pH 8.5) reveal that it is all transformed to N-acetylethanolamine within 23 hours. This short lifetime allows speculation regarding the origin of 2-acetamidoethyl diisopropyl phosphate isolated from the reaction of the base with diisopropyl phosphorofluoridate. (Author)

Descriptors :   (*ORGANIC PHOSPHORUS COMPOUNDS, SYNTHESIS(CHEMISTRY)), (*OXYGEN HETEROCYCLIC COMPOUNDS, PHOSPHORYLATION), (*NITROGEN HETEROCYCLIC COMPOUNDS, PHOSPHORYLATION), CHLORINE COMPOUNDS, AMIDES, MOLECULAR STRUCTURE, NUCLEAR MAGNETIC RESONANCE, CANADA

Distribution Statement : APPROVED FOR PUBLIC RELEASE