Electroreduction of (1S,2S)-2-amino-1-(4-nitrophenyl)-propane-1,3-diol derivatives. Behaviour of electrogenerated species and applications to organic synthesis

Hydroxylamines electrogenerated from (1S,2S)-2-amino-1-(4-nitrophenyl)-propane-1,3-diol derivatives (derivatives of p-nitrophenylserinol) are unstable in methanol–acetate buffer and practically stable in acetonitrile–aqueous acetate buffer. This latter medium was used to carry out subsequent reactions in situ involving the triacetylated p-hydroxylaminophenylserinol and various reagents. An azoxy compound was the major product isolated after reaction with maleic or phthalic anhydrides. In contrast, a benzoxazine dione was normally obtained with phthaloyl dichloride and a N-sulphonylated hydroxylamine was produced with p-toluenesulphonyl chloride.