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Thermolysis and photolysis of arylchlorodiazirines in allyl bromide

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p-Chlorophenylchlorocarbene reacts with allyl bromide to form the expected cyclopropanes. In the case of p-nitrophenylchlorocarbene, a small amount of insertion product is also formed in addition to the cycloadducts. The formation of the insertion product is attributed to the attack of the carbene on the bromine atom followed by intramolecular allylic rearrangement.

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Bonneau, R., Grobys, M., Liu, M.T.H. et al. Thermolysis and photolysis of arylchlorodiazirines in allyl bromide. Res. Chem. Intermed. 20, 141–148 (1994).

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