Alkylation of ambident ions derived from phosphoric–carboxylic imides. N-Benzoyl-O,O-dimethyl-O-ethylphosphorimidate and E/ZO-ethyl-N-(dimethylphosphoryl)benzimidate

Abstract

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-elhyl-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.