7007-02-5

Upstream product

• 813-77-4 Dimethyl chlorophosphate 
• 5961-59-1 N-methyl-N-(4-methoxyphenyl)amine 
• 2101-87-3 p-methoxy-phenylazide 
• 7006-87-3 (4-Methoxy-phenyl)-imidophosphorsaeure-trimethylester 

Downstream Products

• 25627-05-8 Dimethyl-N-<4-methoxy-phenyl>-phosphoramidat 
• 33675-68-2 N-(4-methoxyphenyl)-N-methyl-benzamide 
• 121884-87-5 C₁₆H₁₈NO₅P 

Relevant academic research and scientific papers

Lewis acid or alkyl halide promoted rearrangements of phosphor- and phosphinimidates to N,N-disubstituted phosphor- and phosphinamidates

In this paper, we describe the synthesis of N,N-disubstituted phosphor- and phosphinamidates via alkyl halide or Lewis acid catalyzed rearrangements of phosphor- or phosphinimidates. Furthermore, we introduce a novel one-pot procedure for the synthesis of N,N-disubstituted phosphoramidates which prevents the isolation of potentially explosive alkyl azide derivatives. In this reaction sequence, several alkyl halides are converted in situ into the corresponding azides and reacted with phosphites to generate phosphorimidates. Final addition of a catalytic amount of Lewis acid to the mixture affords the N,N-disubstituted phosphoramidates in good to excellent overall yields. 1 Introduction 2 Synthesis of N,N-Disubstituted Phosphor- and Phosphinamidates 2.1 Alkyl Halide Catalyzed Rearrangement of Phosphin- and Phosphorimidates 2.2 Lewis Acid Catalyzed Rearrangement of Phosphin- and Phosphorimidates 2.3 One-Pot Procedure for the Formation of N,N-Disubstituted Phosphoramidates from Alkyl Halides 3 Conclusion. Georg Thieme Verlag Stuttgart - New York.

PHOSPHORYL TO CARBONYL MIGRATION OF AMINO GROUPS IN MIXED ANHYDRIDES. THE EFFECT OF N-SUBSTITUENTS

The rates of fragmentation of mixed anhydrides (MeO)(p-X-C6H4NMe)P(O)OC(O)Ph (1) (X=MeO, H, Cl, CF3) giving carboxyamides PhC(O)NMe(C6H4-X-p) were measured in CDCl3 at 70 deg C.The reaction constant ρ=+0.85 was obtained.The magnitude of ρ is taken as an indication of low sensitivity of rate to polar effects of substituents (in agreement with the concerted mechanism postulated), and its positive sign suggests that the cleavage of the P-N bond is more advanced in the transition state than is the formation of the N-C bond.

Electronic and Steric Effects in Arylphosphoramidates and Phosphorimidates as Monitored by Carbon-13 Nuclear Magnetic Resonance

13C NMR chemical shifts and 13C-31P couplings are reported for ten arylphosphoramidates and five arylphosphorimidates.The para-carbon chemical shifts in the phosphoramidates are interpreted in terms of substantial nitrogen lone pair delocalization into th