Tetradecyltrimethylammonium permanganate : a novel potassium permanganate derived reagent for trans-dichlorination, trans-dibromination and cis-dihydroxylation of olefins

Abstract

Reactivity of KMnO 4 has been modified by converting it into long chain quaternary ammonium permanganate salt, viz., tetradecytrimethylammonium permanganate (TDTAP). This new versatile, stable reagent has been utilised for chemoselective and stereoselective trans-dichlorination and dibromination of a variety of alkenes. Use of this reagent for vicinal dihydroxylation of alkenes in a two phase solvent system has also been demonstrated. The mechanism for the trans-dichlorination reaction and the nature of the reacting species has been proposed.