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Communication | Special issue | Vol 7, No. 2, 1977, pp.895-905
Published online, 1st January, 1970
DOI: 10.3987/S-1977-02-0895
Synthesis and Ring Expansion of 3-Methyl-3-vinyl-2-dimethylamino-1-azirine

Léon Ghosez,* André Demoulin, Michel Henriet, Etienne Sonveaux, Maurice Van Meerssche, Gabriel Germin, and Jean-Paul Declercq

*Laboratoire de Chimie Organique de Synthése, Université de Louvain, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium


The reaction of 1-chloro-1-dimethylamino-2-methylbuta-1,3-diene with NaN3 gave directly the title 2-amino-1-azirine (I) and molecular nitrogen. (I) thermally rearranged in the vapour phase to give an aminocarbene resulting from C-C bond cleavage. This carbene cyclised to form an aminopyrrole. With dimethylacetylenedicarboxylate, (I) gave a seven-membered heterocycle resulting from C3-N bond cleavage and cyclisation at the terminal vinylic carbon atom.