Reaction of 1-arylpropenyl-lithium with t-alkyl bromides. The influence of substituent electronic effects and additives on the course of the reaction

Abstract

The reaction of 1-arylpropenyl-lithium (1a–c) with t-alkyl bromides proceeds by either a nucleophilic substitution or single electron transfer mechanism, the preferred pathway being a function of electronic substituent effects and the absence or presence of tetramethylethylenediamine or hexamethylphosphoramide.