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The synthetic route to mixed phosphoric-carboxylic imides (1) via the N-acylation of phosphoramidates was investigated. The reaction of PhC(O)X (X=Br, Cl, F) with conjugate base of (EtO)2P(O)NHMe (2) yields three products: PhCO2Et (3), PhC(O)NHMe (4) and (PhCO)2NMe (5). (4) and (5) are formed via the initial rapid formation of (1), while (3) results from the ElcB reaction of (2). The attack of various nucleophilic species at mixed imide (1) was studied, and the possible mechanisms of the P[sbnd]N bond cleavage, followed by the transfer of nitrogen from phosphoryl to the carbonyl centre, are discussed.
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HENDRICKSE et al. (1984) studied this question.
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