P. O'neill, A. F. Hegarty
Jul 1, 1992
Citations
0
Influential Citations
5
Citations
Journal
Journal of Organic Chemistry
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