Chiral oxiranes are converted into chiral aziridines viaβ-hydroxyalkly aryl sulfides and then β-tosylaminoalkyl aryl sulfides without loss of optical purity and with overall retention of configuration.
Thioethers bearing an optically active secondary alcohol were desulfurized with Raneynickel — sodium hypophosphite — acetate buffer system to give optically active alcohols without racemization in high yields. This Raneynickel combination system exhibited a unique desulfurization of benzylthio or phenylthio group in the presence of benzyl ether.