Journal
TETRAHEDRON LETTERS
Volume 47, Issue 20, Pages 3341-3344Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2006.03.103
Keywords
phosphonate-phosphate rearrangement; retro-Abramov reaction; stcreochemistry; nucleophilic substitution; reaction mechanism
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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.
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