Oxidative cleavage of the C-C bond in processes involving the heteroaromatization of 9R-sym-nonahydro-10-oxa(chalcogena)anthracenes

Autor: Blinokhvatov, A. F., Berberova, N. T., Archegova, A. S., Klimov, E. S., Shpakov, A. V., Okhlobystin, O. Yu.
Zdroj: Chemistry of Heterocyclic Compounds; July 1991, Vol. 27 Issue: 7 p711-715, 5p
Abstrakt: The reaction of 9-(2-methoxyphenyl)- and 9-(2-thienyl)-sym-nonahydro-10-selena(thia)anthracenes with trifluoroacetic acid causes their heteroaromatization with the elimination of substituents from the ? positions of the heterorings. A similar transformation of these compounds, as well as their oxygen and 9-benzyl-substituted analogs, occurs during anode electrochemical oxidation. The stepwise character of the cleavage of the C-C bond, which includes one-electron oxidation of the chalogenapyrans and subsequent fragmentation of the cation-radical intermediates, is substantiated.
Databáze: Supplemental Index