Stereochemistry of photosolvolysis of quaternary benzylammonium salts in hydroxylic solvents

Abstract

The photosolvolysis of optically active 1-phenyl-ethyltrimethylammonium iodide in water or methanol is characterised by extensive racemisation acompanied by some net configurational inversion; the quaternary salt recovered from incomplete reaction in water has fully retained configuration at carbon, while analogous retention at nitrogen is observed in similar experiments in methanol with appropriately chosen related salts.