N-Allyl-4-chloro-1,8-naphthalimide reacts normally with bromine to give the corresponding N-(2,3-dibromopropyl) compound. Changing the substituent at the 4- position to an alkylamino group completely alters the outcome of the reaction, which now gives the N-allyl-4-alkylamino-3-bromo-1,8-naphthalimide, where electrophilic aromatic substitution has occurred in preference to simple addition to the alkene. A mechanism for this transformation that involves anchimeric assistance from the imide oxygens will be presented, along with evidence for the involvement of an intermediate based on a new heterocyclic skeleton.

Aromatic bromination in preference to addition to an alkene

253rd National Meeting (2017)

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