121843-91-2Relevant articles and documents
Decomposition of Levuglandin E2. Dehydration and Allylic Rearrangement Products
Iyer, Rajkumar S.,Miller, Donald B.,Salomon, Robert G.
, p. 3175 - 3180 (2007/10/02)
In aqueous solutions at 37 deg C the β,υ-unsaturated δ-hydroxy aldehyde functional array in levuglandin E2 (LGE2) readily eliminates water to give an α,β,γ,δ-unsaturated aldehyde, anhydro levuglandin E2 (AnLGE2), in competition with allylic prototropic shift to give an α,β-unsaturated δ-hydroxy aldehyde, Δ9-LGE2.The allylic isomerization is catalyzed by H2PO4-, perhaps by a bifunctional mechanism involving both proton acceptance by and donation from the catalyst.Thus, by appropriate adjustment of buffer concentration, the product distribution can be altered in a synthetically useful manner.Unexpectedly, the dehydration is not catalyzed by acid under the conditionsexamined (pH 2.8-8.0) and LGE2 is most stable at pH 3-4.
