Stereochemistry of 1-hydroxyphosphonate-phosphate rearrangement.: Retention of configuration at the phosphorus atom

1-Hydroxyphosphonate 1 in the presence of triethylamine in acetonitrile solution undergoes irreversible rearrangement to phosphate 2 and reversible retro-phospho-a Idol (retro-Abramov) reaction. The X-ray structures for 1 and 2 revealed that the phosphonate-phosphate rearrangement occurs with retention of configuration at the phosphorus atom. (c) 2006 Elsevier Ltd. All rights reserved.