American Chemical Society
ol060519l_si_001.pdf (242.36 kB)

Facile Dephosphonylation of β-Ketophosphonic Acids:  Mechanistic Studies

Download (242.36 kB)
journal contribution
posted on 2006-08-03, 00:00 authored by Michael J. Hawkins, Eugene T. Powell, Gregory C. Leo, Diane A. Gauthier, Michael N. Greco, Bruce Maryanoff
We have found that β-ketophosphonic acids can undergo facile dephosphonylation under fairly mild conditions. The rate of dephosphonylation is dependent on the electronic nature of the substituent on the carbon atom α to phosphorus, with electron-withdrawing groups accelerating the process. 31P NMR studies were used to probe the mechanism for the process.