7006-87-3Relevant academic research and scientific papers
Lewis acid or alkyl halide promoted rearrangements of phosphor- and phosphinimidates to N,N-disubstituted phosphor- and phosphinamidates
Wilkening, Ina,Del Signore, Giuseppe,Ahlbrecht, Wiebke,Hackenberger, Christian P. R.
experimental part, p. 2709 - 2720 (2011/10/18)
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.
A nitrogen-15 nuclear magnetic resonance study of N-aryl phosphoramidates and phosphorimidates
Buchanan, G. W.,Morin, F. G.,Fraser, R. R.
, p. 2442 - 2446 (2007/10/02)
15N nuclear magnetic resonance chemical shifts and one-bond 15N-31P couplings are reported for a series of five N-arylphosphoramidates and four N-arylphosphorimidates.Results are interpreted in terms of an extensively delocalized N lone pair in the phosphoramidates, with p?-p? donation into the aromatic ring being dominant over p?-d? donation from nitrogen to phosphorus.
