Journal of Organic Chemistry p. 5209 - 5213 (1995)
Update date:2022-08-16
Topics:
Ruel
Bouvier
Young
The addition reaction between the potassium anion of dialkyl phosphites and acid chlorides at low temperature produced tetraalkyl 1- hydroxybisphosphonates, whereas the corresponding lithium anion gave mostly the rearranged products tetraalkyl phosphono phosphates. The rate of rearrangement was found to be dramatically accelerated by the presence of bulky substituents at the α-position of the acid chloride. Intermediates arising from the addition of dibenzyl phosphite anion rearranged more readily than those obtained from diethyl phosphite anion, but again less so for the potassium anion reagent.
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