Abstract
Flash vacuum pyrolysis of O-allyl salicylic alkylamides and alkyl esters gives isoindolones and phthalides, respectively, in low (20–40%) yield. The mechanism involves generation of the phenoxyl radical, regiospecific hydrogen-atom transfer from the alkylamide (or alkyl ester) group and cyclisation. A similar sequence was observed with thiophenoxyl radicals.
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