THE REACTION OF SOME 3- AND 4-FLUOROOXETANES WITH ACIDS

Article abstract of DOI:10.1016/S0022-1139(00)83066-3

Several oxetanes prepared from hexafluoroacetone and hydrofluoroolefins were treated with aluminum chloride.Substitution of fluorine by chlorine occured on the 3- and 4-carbon atoms as well as cleavage of the ether leakage to give chloroalkyl carbinols or in, some cases, vinyl carbinols.Individual samples of the cis and trans-3,4-difluorooxetanes formed roughly equivalent amounts of the 3-fluoro-4-chlorooxetane stereoisomers, indicating a common carbonium intermediate.Treatment of the 4-fluorooxetane with sulfuric acid gave a dioxetane, a dioxene and an unsaturated aldehyde.