Reaction of 1-Phenyl-3,4-dichloro-2-aza-1,3-pentadiene with Triethyl Phosphite

摘要

It was shown previously that 3,4,4-trichloroazadiene Ia reacts with trialkyl phosphite with the substitution of chlorine at the C~3 atom and formation of phosphorylated azadiene IIa [1]. Substitution of chlorine at the C~4 atom by the electron-donating methyl group directs the attack of triethyl phosphite at the electrophilic centers at C~3 as well as at C~1 atoms of azadiene Ib. For example, reaction of Ib with triethyl phosphite yields phosphorylated azadiene (Iib, R = Me) (E + Z isomers), mono- and bisphosphorylated derivatives III and IV, and diethyl hydrogen phosphite V in the 0.3 : 0.3 : 1 : 1.2 molar ratio, respectively, along with some unidentified compounds.