The crystalline‐state photoreaction of 1‐azido‐2‐nitrobenzene (1) was investigated by a combination of X‐ray crystallography, IR spectroscopy, electron‐spin resonance (ESR), and by means of theoretical calculations. Upon low‐temperature (80 K) photolysis of 1, the formation of benzofuroxan (2) was directly observed by X‐ray single‐crystal analysis. ESR Measurements at 5 K suggested the presence of a triplet nitrene as an intermediate in the formation of the heterocycle. Temperature‐dependent IR spectroscopy also revealed that another intermediate, trans,trans‐1,2‐dinitrosobenzene, was produced at temperatures below 80 K.
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Takayama et al. (2003) studied this question.
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