[gryzli]

Hi, I am trying to figure out what is the mechanism of oxidation step during synthesis of quinoline (starting with aniline and using iodine as oxidating agent). I know that heterogenic ring is attacked by iodine radical at C2 position to form allyl radical, as in second step on my drawing. Then it could switch into different resonance structure (captodative effect) with electron pair on C2 and radical cation on nitrogen. The last step would be reaction with second iodine radical, where electron pair is formed out of two radical electrons and double bond is formed between C2 and nitrogen (using electron pair from C2). Does that make any sense?