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Treatment of 2-phenyl-1-azirine in cyclohexane with Cu(II) bromide afforded ω-bromoacetophenone azine, but in carbon tetrachloride gave 2-bromomethyl-2,4-diphenyl-2H-imidazole via 2-bromo-3,5-diphenyl-1,4-diazabicyclo[3.1.0]hex-3-ene.
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Hayashi et al. (1975) studied this question.
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