2-Halogeno-3-morpholinothietan 1,1-dioxides. Reactivity in base promoted elimination and ring cleavage

Abstract

The behaviour of some 2-halogeno-3-morpholinothietan derivatives towards basic reagents has been studied. The pattern of ring substitution and the stereochemical relationships between the substituent groups partly determine the reaction paths. The 4,4-dimethyl derivatives undergo hydrogen halide elimination. The 4-unsubstituted or 4-methyl derivatives are structurally prevented from undergoing hydrogen halide elimination when they bear a 3-phenyl group and ring cleavage is then the preferred reaction. Further transformations of these primary products in the reaction medium are described.