Donor-Atom Effects on Relative E2 Rate Constants for Reactions of Anions with Cyclohexyl Bromide

Article abstract of DOI:10.1021/jo00145a053

2-Naphthoxide oxanions <2-NpO(1-)> and carbazole nitroanions react with cyclohexyl bromide in Me2SO solution to give cyclohexene, whereas 9-methylfluorene carbanions <9-MeFl(1-)> give substitution and benzenethiolate thianions give both elimination and substitution.The relative order of E2 rate constants for anions of the same basicity is ArS(1-) > 2-NpO(1-) > Cb(1-) > 9-MeFl(1-).