85014-39-7Relevant academic research and scientific papers
Alkylation of ambient ions derived from phosphoric-carboxylic imides. N-Benzoyl-O,O-dimethyl-O-ethylphosphorimidate and E/Z O-ethyl-N-(dimethylphosphoryl)benzimidate
Mizrahi, Valerie,Hendrickse, Theodore,Modro, Tomasz A.
, p. 118 - 123 (2007/10/02)
The sodium salt of N-benzoyldimethylphosphoramidate was ethylated using triethyloxonium ion or ethyl iodide as alkylating agents.The former reaction gave two oxygen-alkylated products: N-benzoyldimethylethylphosphorimidate and O-ethyl-N-(dimethylphosphoryl)benzimidate.The latter reaction yielded only the carbonyl oxygen ethylation product as a pair of the geometrical (E/Z) isomers.The nmr spectra and fragmentation patterns of the obtained products are discussed.
STRUCTURE - REACTIVITY OF MIXED CARBOXYLIC PHOSPHORIC IMIDES
Mizrahi, Valerie,Modro, Tomasz A.
, p. 141 - 144 (2007/10/02)
The title compounds comprise carboxylic and phosphoric amide functions modified at nitrogen by another acyl group.X2P(O)-NR-C(O)R' (1) X-ray crystallography revealed intramolecular interactions between carbonyl oxygen and phosphorus in (1).Under conditions of electron impact all substrates (1) isomerise to the corresponding O-phosphoryl imidates X2P(O)-O-C(NR)R'.Solvolysis of (1) depends on medium acidity; in neutral media the exclusive attack at phosphorus was observed, while the acid catalyzed solvolysis involves both N-acyl linkages and the reaction proceeds via the carbonyl oxygen protonated intermediate.Hydration parameter treatment was applied to the hydrolysis of (1).Nucleophilic behavior of (1) was studied in alkylation of their conjugate basis derived from secondary substrates (1, R=H).
