SCHEDULED MAINTENANCE
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.
M. Black, J. I. G. Cadogan and H. McNab, J. Chem. Soc., Perkin Trans. 1, 1994, 155 DOI: 10.1039/P19940000155
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