O. N. Bubel

Reaction of acetyloxiranes with acetonitrile

Abstract2-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.

Synthesis, stereochemistry, and isomeric transformations of 4-aryl-5-aroyl-2-methylthio-2-imidazolines

The corresponding 4-aryl-5-aroyl-2-methylthio-2-imidazolines were obtained by the reaction of complexes of cis- and trans-3-aroylaziridines and boron trifluoride with methyl thiocyanate. It is shown on the basis of spectral data that the aziridine ring is opened regiospecifically at the C(2) atom and stereospecifically with inversion of the configuration.

Boron fluorides of cis- and trans-2-aryl-3-aroylaziridines

The reaction of boron trifluoride etherate with cis- and trans-2-aryl-3-aroylaziridines yields the respective complexes in high yield. According to PMR spectral data the methyl group of boron trifluoride trans-1-methyl-3-aroylaziridines is located in syn-position, and in the cis-aziridine complexes in anti-position, to the carbonyl group.

Synthesis and products of hydrolysis of 2-methyl-5-(β-arylacrylyl)-2-oxazolines

The condensation of 2-methyl-5-acetyl-2-oxazolines with p-R-substituted benzaldehydes in the presence of bases gave the corresponding 2-methyl-5-(β-aryl-acrylyl)-2-oxazolines, the hydrolysis of which with hydrochloric acid leads to hydrochlorides of alkyl-substituted 1-(p-R-styryl)-2-acetoxy-3-aminobutan-1-ones. Treatment of the latter with bases gives 1-(p-R-styryl)-2-hydroxy-3-N-acetyl-2, 3-alkylbutan-1-ones.