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The 2-azidobuta-1,3-dienes 10a,b were treated with sulfur dioxide to prepare the 3-azido-3-sulfolenes 11a,b, and with electron-poor dienophiles to generate the Diels–Alder products 12a,b, 13a,b, 14a,b, 15a,b, and 16b. Both types of reactions provide an access to cyclic vinyl azides, which lead to short-lived 2,3-bridged 2H-azirines 18a,b and 20a,b on photolysis. Whereas the highly strained heterocycle...
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...
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