73777-14-7Relevant academic research and scientific papers
SN2 iodide displacement on unsymmetrical cyclic dioxenium salts. A stereoelectronically controlled reaction
Beaulieu, Normand,Deslongchamps, Pierre
, p. 164 - 167 (2007/10/02)
Iodide ion reacts with the cyclic dioxenium salts 1-6 to yield mixtures of iodoester and lactone plus alkyl iodide (Table 1).The formation of iodoester competing with the formation of lactone appears to be an unexpected result.It can, however, be explained by a stereoelectronic effect, similar to the anomeric effect in acetals, which is also responsible for the greater stability of the Z over the E form in dioxenium salts and in esters.
