The Step‐Wise Synthesis of Oligomeric Phosphoramidates. Issue 40 (28th September 2021)

• Record Type: Journal Article
• Authors: Data, Shailja; Leung Wai, Jeffery; Kumar, Saawan; Cameron, Alan J.; Trehet, Manon; Itumoh, Emeka J.; Feld, Joey; Söhnel, Tilo; Leitao, Erin M.
• Is Part Of: European journal of organic chemistry. Issue 40(2021)
• Page Start: 5468
• Page End: 5477
• Publication Date: 2021-09-28
• Subjects: Antimicrobial activity -- Lithiation -- Phosphoramidates -- Pnictogens -- Salt elimination; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202101062
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : Ex(P−N)ding the chain . Salt elimination and lithiation strategies were employed in the step‐wise synthesis of oligomers with P−N linkages having potential as environment friendly flame retardants due to their lack of anti‐microbial activity.