ACTION DU CHLORURE D'ACETYLE ET DE L'ANHYDRIDE ACETIQUE SUR LE NITRONATE DE LITHIUM DERIVE DU PHENYL-2 NITROETHANE. REACTIVITE ELECTROPHILE OU DIPOLAIRE, EN FONCTION DU MILIEU, DE L'OXYDE DE NITRILE INTERMEDIAIREMENT FORME

Article abstract of DOI:10.1016/S0040-4020(01)87537-2

The lithium nitronate salt derived from 2-phenyl nitroethane reacts with acetic anhydride and with acetyl chloride to give an intermediate nitrile oxide.Depending on the protonating character of the medium, this latter can react either as a 1,3 dipole to give the furoxan or, in the presence of a dipolarophile, the corresponding adduct; or as an electrophile leading to the chlorooxime or to derivatives of benzohydroxamic acid.The formation of the nitrile oxide, by loss of acetic acid from a nitronic-acetic mixed anhydride, appears to be the most plausible reaction pathway accounting for the above observations.