Photolysis of open-chain 1,2-diazidoalkenes: generation of 2-azido-2H-azirines, formyl cyanide, and formyl isocyanide |
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| Authors: | Klaus Banert Joseph Rodolph Fotsing Hans Peter Reisenauer Günther Maier |
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| Institution: | a Institute of Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, 09111 Chemnitz, Germany
b Institute of Organic Chemistry, Justus-Liebig-University Giessen, Heinrich-Buff-Ring 58, 35392 Giessen, Germany |
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| Abstract: | Solutions of several open-chain 1,2-diazidoethenes were photolyzed to yield 2-azido-2H-azirines, which were identified by NMR spectroscopy at low temperature. On prolonged irradiation or warm-up of the NMR solutions, these heterocycles lost a second molecule of nitrogen to be cleaved into two fragments of cyano compounds. In the case of (Z)-2,3-diazidocinnamaldehyde, the formation of formyl cyanide was detected by IR spectroscopy when the photolysis was performed in argon matrix. The latter substance was rearranged to formyl isocyanide on irradiation. This new species was characterized by comparison of its experimental and calculated (B3LYP/6-311+G∗∗) IR spectrum. |
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| Keywords: | Azides Azirines Formyl isocyanide Matrix isolation Nitriles Photochemistry |
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