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Paper | Special issue | Vol 40, No. 1, 1995, pp.271-278
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S22
■ 1,3-Dipolar Cycloaddition of Nitrones and Nitrile Oxides to 5,5-Dimethyl-3-methylenepyrrolidine-2-thione

Lubor Fisera, Libuse Jaroskova, Iveta Matejkova and Heinz Heimgartner

*Department of Organic Chemistry, Slovak University of Technology, SK-812 37 Bratislava, Slovakia

Abstract

A simple synthesis of title compound (3) and a number of different cycloadditions are described. C-Aroyl- and C,N-diphenylnitrones react regio- and stereoselectively to the C=C exocyclic double bond of 3, to give only spirocycloadduct (10). On the other hand, C-phenyl-N-methylnitrone gives a mixture of diastereomeric spirocycloadducts (10) and (11). Nitrile oxides undergo 1,3-dipolar cycloaddition both to the exocyclic C=C and C=S double bonds with subsequent cycloreversion and formation of spiro-lactams (6). The appropriate spiro-thiolactams (8) were synthetized by treatment of 6 with Lawesson’s reagent.