M. Black et al., PYROLYSIS OF O-ALLYL SALICYLIC AMIDES AND ESTERS, AND RELATED-COMPOUNDS - FORMATION OF ISOINDOLONES AND PHTHALIDES, Journal of the Chemical Society. Perkin transactions. I, (2), 1994, pp. 155-159
Flash vacuum pyrolysis of O-allyl salicylic alkylamides and alkyl este
rs gives isoindolones and phthalides, respectively, in low (20-40%) yi
eld. The:mechanism involves generation of the phenoxyl radical, regios
pecific hydrogen-atom transfer from the alkylamide (or alkyl ester) gr
oup and cyclisation. A similar sequence was observed with thiophenoxyl
radicals.