Reactivity of aminophosphonic acids. 3. Reaction with hydrogen peroxide

Abstract

The reactions of aminoalkylphosphonic acids with hydrogen peroxide in 2 M KOH and 2 M H₂SO₄ solutions were investigated. The formation of phosphate ion (P_i), as a result of the hydrogen peroxide-promoted cleavage of the C_α-P bond, was observed in a few cases. The dephosphonylation of aminoalkylphosphonic and 1-(N-alkylamino)alkylphosphonic acids were found to occur at a moderate rate in basic solution and was not observable in acidic solution. 1-(N,N-dialkylamino)-alkylphosphonic acids in alkaline solutions were oxidized into the corresponding N,N-dialkyl-N-oxide derivatives.

Graphical Abstract

Keywords:

• Amino acids
• aminophosphonic acids
• hydrogen peroxide
• dephosphonylation
• oxidative cleavage of the P-C bond