Synthesis and NMR Characterization of Two Novel Anthracene-Derived BIS-Aminophosphonates. Basic Hydrolysis of Some Aminophosphonate Derivatives

Abstract The synthesis of two novel bis-aminophosphonates bearing anthracene rings – bis[N- methyl(diethoxyphosphonyl)-1-(9-anthryl)]benzidine (3) and 4,4′-bis[N-methyl(diethoxy-phosphonyl)-1-(9-anthryl)]diaminodiphenylmethane (4) – via the Kabachnik–Fields reaction is reported. The compounds have been characterized by elemental analysis, TLC, IR, NMR (1H, 13C, 31P) and fluorescent spectra. The reaction leads to a mixture of the two possible forms (meso and racemic), with predominant formation of one of the diastereomers. The recrystallized compounds 3 and 4 consist of only one diastereomer. A racemization at the chiral centers and a cleavage of the C-P bond are observed in the alkaline hydrolysis of the new compound 4 and three previously described aminophosphonate derivatives 5–7. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.