ORIENTATION IN BASE-PROMOTED DEHYDROHALOGENATION OF N-(CHLOROBENZYL)-NORMAL-BUTYLAMINE

Although the mechanisms of olefin formation by basepromoted dehydrohalogenation have been extensively investigated,3, 4 the removal of hydrogen halide across C-N bonds has received little attention. The only kinetic studies of imine-forming dehydrohalogenation involve the reactions of alkyldifluoroamines, RCH2NF2, in water-diglyme at 25-75 °C reported by Braumann and Hill.5, 6 In contrast to the strongly basic conditions required for alkene formation by dehydrofluorination of closely related 1, 1-difluoro-2-arylethanes,7 water was a sufficiently strong base to induce eliminations from the alkyldifluoroamines. These observations underscore the marked facility of carbon-heteroatom multiple bond forming eliminations when compared with analogous processes leading to alkenes or alkynes. © 1979, American Chemical Society. All rights reserved.