The Step-Wise Synthesis of Oligomeric Phosphoramidates

Shailja Data, Jeffery Leung Wai, Saawan Kumar, Alan J. Cameron, Manon Trehet, Emeka J. Itumoh, Joey Feld, Tilo Söhnel, Erin M. Leitao

Research output: Contribution to journalArticlepeer-review


In this study, the step-wise synthesis to a series of higher phosphoramidates was explored, affording compounds containing N−P−N, symmetric and asymmetric P−N−P and P−N−P−N−P linkages. Salt elimination and lithiation strategies were employed to create the new P−N bonds. It was found that the steric bulk and electronic contribution of the substituents on the P(V) centers were important factors to the success of the reactions. The oligomeric phosphoramidates were characterized by multinuclear NMR and IR spectroscopies as well as ESI mass spectrometry. A selection of the synthesized P−N oligomers were evaluated for their antimicrobial activity against E.coli, S.aureus, C.albicans, and A.fumigatus at varying concentrations. The results suggest their potential use as environmentally friendly fire retardants as the minimal inhibitory concentration (MIC) value for all the compounds was found to be >128 μM, indicating that the compounds do not have any detectable antimicrobial activity.

Original languageEnglish
Pages (from-to)5468-5477
Number of pages10
JournalEuropean Journal of Organic Chemistry
Issue number40
StatePublished - 26 Oct 2021
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2021 Wiley-VCH GmbH


The authors would like to acknowledge the support provided by the School of Chemical Sciences, University of Auckland and the MacDiarmid Institute. We thank Tatiana Grousto for collecting the single crystal X‐ray diffraction data.

FundersFunder number
School of Chemical Sciences, University of Auckland


    • Antimicrobial activity
    • Lithiation
    • Phosphoramidates
    • Pnictogens
    • Salt elimination


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