IODINE (III) MEDIATED ACETOXY-LACTONIZATION OF UNSATURATED NITRILES

Article abstract of DOI:10.1016/S0040-4020(01)87896-0

4-Pentenenitriles reacted with PhI(OAc)2 in acetic acid, in the presence of 48percent HBF4, at 70 deg C, to afford the dihydro-5-acetoxymethyl-2(3H)-furanones in good yields.Similarly, 3-butenenitriles gave the dihydro-4-acetoxy-2(3H)-furanones, although in lower yields.Parallel experiments showed that, under the same conditions, 4-pentenoic and 3-pentenoic acids reacted much more easily and gave the same acetoxy-lactonization process at room temperature.