Pyrolysis of O-allyl salicylic amides and esters, and related compounds: formation of isoindolones and phthalides
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.