Base-Catalyzed Dehydrogenation of 2,2',4,4',6,6' - Hexanitrobibenzyl by Quinones

摘要

The dehydrogenation of 2,2',4,4',6,6'-hexanitrobibenzyl by quinones takes place only in basic median, particularly in hexamethylphosphoramide alone or in dimethylformamide in the presence of a suitable base. A study of the reaction mechanism indicates that hydrogen is transferred heterolytically and that the abstraction of H(-) occurs only after removal, or partial removal, of H(+). The yield of 2,2',4,4',6,6'-hexanitrostilbene was highest with 2,3-dichloro-5,6-dicyanobenzoquinone and generally decreased with declining quinone redox potential. (Author)