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Paper | Regular issue | Vol 57, No. 7, 2002, pp.1257-1264
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9490
A New Synthesis of 1,2-Diazetines via Simple Cycloacylation Reactions

Daniela Pufky, Rainer Beckert,* Manfred Döring, and Olaf Walter

*Institute for Organic and Macromolecular Chemistry, Friedrich Schiller University Jena, D-07743 Jena, Lessingstr. 8, Germany

Abstract

Several new 1,2-diazetines (4a-e) were synthesized via simple cycloacylation reactions of various monoalkylhydrazines (5a-c) with bis-imidoyl chlorides of oxalic acid (1). An X-Ray crystal structure analysis obtained from single crystals of 4a reveals an additional double bond in the 4-membered ring system. Treatment of these heterocycles with strong bases formed delocalized anions (6) which can be methylated giving 1,2-disubstituted diazetidines (7a,b). Alternatively, the latter derivatives can be synthesized via a cycloacylation employing 1,2-dimethylhydrazine and bis-electrophiles (1).