Synthesis of Dibenzylic Diselenides from Elemental Selenium and Benzylic Quaternary Ammonium Salts

Abstract

Abstract Abstract : Substituted dibenzyl diselenides are synthesized in good yields (74–91 %) by S N 2 nucleophilic substitution of benzylic trimethylammonium salts and diselenide dianion (Se 2− ), in situ generated from elemental selenium, under basic conditions. Highly enantiopure dibenzylic diselenides (95–98 % ee) with reverse configurations to their enantioenriched quaternary ammonium salts are obtained, if benzylic quaternary ammonium salts, synthesized from enantiomerically enriched amines, are used.