MoO-11


THE PAYNE REARRANGEMENT AND EXTENSION TO HIGHER HOMOLOGUES

Suresh Dua, John M. Hevko, John H. Bowie, Mark S. Taylor and Mark A. Buntine

Department of Chemistry, The University of Adelaide, South Australia, 5005


The Payne rearrangement is an anionic process in which nucleophilic substitution causes equilibration between to ethylene oxide systems. A combination of product ion, labelling (2H and 18O) and computational studies, shows that the Payne rearrangement (shown below) competes with formation of an oxetane ring system in the gas phase.

Figure


Corresponding processes occurring for oxetan and tetrahydrofuran analogues of the Payne rearrangement will be described.