Facile dephosphonylation of beta-ketophosphonic acids: mechanistic studies.
[reaction: see text] We have found that beta-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 alpha to phosphorus, with electron-withdrawing groups accelerating the process. 31P NMR studies were used to probe the mechanism for the process.
Hawkins
Michael J
MJ
Research & Early Development, Johnson & Johnson Pharmaceutical Research & Development, Spring House, Pennsylvania 19477-0776, USA.
Powell
Eugene T
ET
Leo
Gregory C
GC
Gauthier
Diane A
DA
Greco
Michael N
MN
Maryanoff
Bruce
B