Abstract
The stereochemical course of diastereomeric 1-cyclohexyl-2-phenyl-3-azetidinyl mesylates (IVa and Va) was investigated with nucleophilic reagents. The retention of the configuration in these reactions and ring contracted products in some cases of reactions of IVa were observed. The presence of 1-azabicyclobutonium ions (VII and VIII) as intermediates in these reactions has been proposed from these results. The stereochemistry of 3-substituted azetidines obtained by nucleophilic reactions via IVa and Va was established by chemical evidence and nuclear magnetic resonance studies with a shift reagent, Eu (DPM)3.
