ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

1,3-Dipolar Cycloaddition of Heterocycles. 32. Cycloadditions of Nitrones to N-(2,6- dialkylphenyl)maleimides

L. Jarošková, M. Konopíková, and Ľ. Fišera

Department of Organic Chemistry, Faculty of Chemical Technology, Slovak Technical University, SK-812 37 Bratislava

Abstract: The 1,3-dipolar cycloadditions of nitrones to N-(2,6-dialkylphenyl)maleimides give mainly anti-adducts. The Z/E isomerization of nitrones and the sterically preferred exo attack avoiding the repulsions between N-arylmaleimide and N-phenyl moiety of nitrone was proposed. The reaction of N-(2-ethyl-6-methylphenyl)maleimide with nitrone gave, due to hindered rotation, two or four types of diastereoisomers characterized by different spatial arrangement of alkyl groups vs. bridge-head hydrogen atoms.

Full paper in Portable Document Format: 481a35.pdf

Chemical Papers 48 (1) 35–39 (1994)