Abstract
The title compounds, including the parent 3-azido-2H-azirine, were generated by low-temperature photolysis of the corresponding 1,1-diazidoethenes, and characterised not only by trapping reactions, but also by direct detection using NMR and in situ IR spectroscopy.
Highlights
Successful synthesis of an unknown class of compounds, 3-azido-2H-azirines, which are implicated as highly reactive intermediates in the thermolysis of the corresponding 1,1-diazidoethenes, has been performed
Unimolecular reactions of 1, 2a and 2b induced by thermolysis or photolysis were investigated intensively.[7,8,10,11]
Encouraged by successful characterisation of azirine 5, we were highly motivated to generate the parent compound, 3-azido-2H-azirine (16), which requires the synthesis of unknown 1,1-diazidoethene (4)
Summary
Successful synthesis of an unknown class of compounds, 3-azido-2H-azirines, which are implicated as highly reactive intermediates in the thermolysis of the corresponding 1,1-diazidoethenes, has been performed. These elusive heterocycles have been detected and characterised by low-temperature NMR and in situ IR spectroscopy. 3-azido-2H-azirine, has been observed via low-temperature photolysis of 1,1-diazidoethene, as a highly reactive species with a half-life period of only 12 min at −40 °C.
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