REACTION OF ACETYLOXIRANES WITH ACETONITRILE

Article abstract of DOI:10.1007/BF00506574

2-Acetyloxiranes react with acetonitrile in the presence of equimolar amounts of Lewis acids.It was established that the use of boron trifluoride etherate or sulfuric acid as the catalyst leads to 2,7- and 3,6-diepoxy-1,5-dioxocanes, the use of aluminum trichloride, as well as stannic chloride, leads to the corresponding chlorohydrins, while the use of gaseous boron trifluoride leads to 2-oxazolines in satisfactory yields.It is shown that the reaction is regio- and stereospecific and that the resulting substituted 2-methyl-5-acetyl-2-oxazolines have a cis configuration.