Hydrolytic instability of C-F bonds in 2,2,2-trifluoroethyl-phosphinic acid systems: formation of carboxymethylphosphinic acid derivatives.

ABSTRACT: The trifluoromethyl group in 2,2,2-trifluoroethylphosphonic acid remains stable against hydrolysis. However, in contrast, 2,2,2-trifluoroethylphosphinic acid and its derivatives display unexpectedly low hydrolytic stability of the C-F bond in alkaline solutions. When treated with bases such as alkali metal hydroxides or tetramethylammonium hydroxide, these compounds undergo hydrolysis of the R-CF₃ group, producing R-COO^- and F^- quantitatively. This phenomenon is easily observed using ¹⁹F NMR spectroscopy, which provides a clear analytical signature of the transformations. Although the resulting carboxymethylphosphinic acid derivatives somewhat resemble malonic or phosphonoacetic acid derivatives, they demonstrate remarkable stability in both stro

SUBMITTER: Koucky F 

PROVIDER: S-EPMC12691380 | biostudies-literature | 2025 Dec

REPOSITORIES: biostudies-literature