Abstract
Bis(pentachlorophenyl)acetic acid esters were synthesized from the α-hydroxydiaryl acetate esters 13 free radicals 16 formed on homolytic cleavage of the α-chloro compounds 14.The acid 8 underwent rapid decarborylation in basic solution (e.g., Et 3 N in THF) but could be dehydrated to the corresponding ketene 17. Nucleophilic addition to the ketene provided a route to the corresponding amides (21 and 19) and nitrile 20, the enolates of which underwent ready oxidation to the corresponding stable free radicals 16, 22, and 23
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